That One Boss: Pokémon

Behold the tales of Pokémon bosses, Gym Leaders, and Grand Masters for whom laughter at the player's expense flow more readily than the water in the Eclo Wastes. To make a long story short, these are the reason why Gym Guides exist.

NOTE: Final Bosses and Wake Up Call Bosses are not allowed unless they're overly difficult by their standards. Bonus Bosses are not allowed; they're optional and have no standards for difficulty. Battle Frontier/Pokémon World Tournament/challenge area bosses count as Bonus Bosses, so same rules apply.


Generation I: Red, Blue and Yellow, plus FireRed and LeafGreen
  • Brock. His Rock-type Pokemon have high Defense and resistances for the level you must face him as, making him a particular sturdy Wake-Up Call Boss depending on which Pokemon you have chosen as a starter. It doesn't help that most of the Pokémon you can catch before then will be weak or ineffective against him.
    • This is much worse in Pokemon Yellow, as your starter, your beloved Pikachu, will most likely have no reliable strategy to deal with any of his Pokemon 1-vs-1 bar Potion spamming until level 20, when he gets Slam and his absurdly higher level will most likely be strong enough to take his Pokemon down with several non-effective hits. They actually realized how unfair Brock would be, and so they offered a number of other options for players willing to explore, mostly by adding Mankey to Route 22.
    • FireRed and LeafGreen has all of Brock's Pokemon know Rock Tomb, making him more of a threat if you chose Charmander. However, if you taught your Charmander Metal Claw, he becomes laughably easy.
  • In the original Red/Blue, there's a Rocket in Mt. Moon with a Level 16 Raticate that knows Hyper Fang and will likely be faster than you. This Rocket is regarded as one of the hardest trainers in the game in relation to when he shows up, and the remakes gave him a weaker Rattata and Sandshrew instead.
  • Misty's Starmie is effectively almost guaranteed to be faster and stronger than anything you will have at that point and it does very high damage even for mons that resist Water. In FireRed and LeafGreen, her Starmie has switched BubbleBeam for Water Pulse which confuses you about once every three turns it's used.
  • Lt. Surge in Yellow has only one Pokémon, which is his Raichu. Easy, right? Wrong. First off, it knows Thunderbolt, which hits incredibly hard, especially at this part of the game, and it hits even harder than usual due to STAB. And to top it off, Raichu is at level 28, much higher than anything you've faced at this point in the game. It also has Mega Punch and Mega Kick, both of which hit incredibly hard and will do a number on Pokémon with lackluster defenses. To make it even harder, Raichu is one of the fastest Pokémon in the game, meaning that you probably won't have anything fast enough to hit it first. Unless you managed to grab a Diglett or Dugtrio from the nearby tunnel.
  • Erika might not seem like much trouble, but if she manages to get the first attack in, be prepared for her Victreebel to spam the single most annoying attack of Gen 1: Wrap. Unlike the version of the attack you're now familiar with, Gen 1 Wrap prevented your Pokémon from taking any actions while they were caught. And guess what she'll do the moment your Pokémon is free from her Wrap attack. That's right, use Wrap again, preventing you from doing anything more than watching as the attack chips away your helpless Pokémon's health at a painfully slow pace to add insult to injury, and God forbid she manages to paralyze your Pokémon while they're suffering Wrap. You'll essentially be stuck in an infinite juggle. On the other hand, if you get the first attack in, this battle will be very easy if you're a Fire, Flying, or Ice-type.
  • Koga in Yellow. In addition to getting a huge level spike from Red and Blue, Koga now uses the strategy of Double Team + Toxic to stall out your Pokemon. His Level 50 Venomoth (which is likely stronger than anything you have at that point by at least ten levels) is more than capable of tanking most anything you can actually hit him with, and its Psychic attack can usually knock out most of your team in two hits. If you thought ahead and brought a Psychic Pokemon into battle, it also knows Leech Life, one of the rare moves in Generation 1 that is super-effective against psychics, plus it heals Venomoth! In FireRed and LeafGreen; both of his Koffing and Weezing have the Levitate ability to turn their Ground-type weakness into an immunity, and Muk would spam Acid Armor and Minimize to increase its already strong defenses.
  • Sabrina at Gen 1. Her team of Psychic-type Pokémon is fifteen to eighteen (depending on which version you're playing) levels higher than the last gym leader. It doesn't help much that Psychic-types were also extremely overpowered in Gen I due to a glitch making them immune rather than weak to Ghost, contrary to in-game advice and Nintendo's own guides, and a poorly-balanced elemental system in which Psychic's only weakness, Bug, had lackluster Pokemon and moves. To rub salt in the wound, the only Ghost types at the time were also part-Poison, creating a vulnerability to Psychic moves. Thank goodness this has been fixed in the remakes.
  • Lorelei in the FRLG remakes is perhaps the largest leap in difficulty from her original RBY incarnation. Her previous Stone Wall speed-bump team is now filled to the brim with Ice Beam, Surf and Hail and most are tough enough to soak at least two hits from your pokemon while killing them in the same amount of hits with powerful STAB attacks. Barring bringing a Lapras with Water Absorb and Thunderbolt, very few pokemon in the game can set up a whole-team sweep on her like you can on Bruno, Agatha or Lance, and a single bad freeze can leave your whole strategy dead in the water.
  • Lance in RBY. All of his Pokémon know Hyper Beam. In RBY, Hyper Beam does not require a recharge turn if it defeats an opponent, which is not hard for it to do in one hit considering this attack has a base power of 150 and most of Lance's Pokémon have incredibly high Attack.
    • If you get the first strike every time and use Ice Beam and/or Blizzard though, Lance becomes an absolute joke. Oh, and he opens with Gyrados, which has 4x weakness to electric attacks.
  • When you face Blue in the Champion Battle in Gen 1, most of his team is actually fairly easy, but his Alakazam, despite being his lowest-level Pokémon, is the exception. Aside from its game-breaking Psychic type (see Sabrina's entry above), Alakazam is extremely fast and its Special Stat is even more monstrous, which it puts to good use with Psychic and Psybeam. It can also cover its low Defense with Reflect and heal itself with Recover.

Generation II: Gold, Silver and Crystal, plus HeartGold and SoulSilver
  • Whitney's Clefairy is for the most part is easy to deal with, but the same cannot be said for the infamous Miltank. It has Rollout, a Rock-type attack that gets stronger every consecutive turn it connects, and lasts up to five turnsnote . At this stage in the game, Rollout can gradually put the hurt on pretty much anything, even if it resists Rock. Miltank also knows Attract, which can infatuate male Pokemon and give them a 50% chance of not attacking every turn, Stomp, a strong STAB attack with a chance of causing flinching, and Milk Drink to restore health. Add to that Miltank is surprisingly fast and has enough bulk to give most physical attackers pause. In HeartGold & SoulSilver, they gave her the ability "Scrappy" (how appropriate) which allows it to hit Ghost-types with Normal-type attacks. On top of that, they gave it a Lum Berry as a hold item, giving it the ability to remove whatever status ailment you inflicted upon it. However, an in-game trainer in the Goldenrod Department Store will swap their female Machop for a Drowzee (or an Abra, in Crystal). It makes the battle much easier as it is immune to Attract, resistant to Rollout, and has super-effective moves.
  • In Gen II's remake, Bugsy's Scyther gained a move called U-Turn, which takes Scyther off the field to protect her from retaliation. The real horror comes from a strategy with Scyther: Once Bugsy's two cocoon Pokémon faint, Scyther has a STAB 70 power Bug-type attack without drawback (and with Scyther's good attack stat spells trouble) and the other attacks get a boost from Technician, Scyther's ability. There's also the fact that Scyther is extremely fast, so you probably won't be able to attack first.
  • Morty's Gengar was already strong, with STAB Shadow Ball, Hypnosis to put you to sleep, Dream Eater to Life Drain sleeping Mons, and Mean Look to prevent switching out. Then HG/SS improved it even further, with Levitate turning its Ground weakness into an immunity, and Shadow Ball running off Gengar's monstrous Special Attack, instead of its inferior Attack meaning that just about anything that doesn't resist it will be floored in one hit, or have most of their health blasted off.
  • Pryce's Dewgong. It has incredible defense, and often opens up with Icy Wind, which will lower your speed after damaging you. Once your speed is lowered, it'll spam Headbutt to make you flinch, and Rest when its HP is low, just to aggravate you. So, it traps you in an endless, hellish cycle of Headbutting and healing, EVERY. CHANCE. IT. GETS.
  • Clair's ace: Kingdra, a dual typed Water/Dragon Pokémon. It's only weak against Dragon-type moves, which you are unlikely to have at this point. Kingdra is packing some serious heat in the form of Surf, Dragon Breath, and Hyper Beam - and it has the stats to use those as well. In HG/SS, Kingdra gets even more brutal, with Surf and Dragon Breath upgrading to Hydro Pump and Dragon Pulse, a held Sitrus Berry, and the Sniper ability, which boosts the damage on Kingdra's critical hits.
  • Karen of the Elite Four in HG/SS. Murkrow can hit Fighting- and Bug-types hard with Pluck, force your Pokemon out with Whirlwind, use a STAB Faint Attack, which never misses, and hit your Pokemon with Sucker Punch. Houndoom was gifted with Nasty Plot to send its already beefy Special Attack through the roof, Vileplume on its own isn't too tough, but Karen is smart enough to anticipate you using a fire type move on it, switching to Houndoom so it will use Flash Fire to buff its Special Attack without even having to use Nasty Plot, Umbreon is very bulky and can use its sluggish speed to its advantage with Payback, and Gengar has Focus Blast and Destiny Bond, the latter of which takes your Pokemon down with Gengar if K Oed the same turn Destiny Bond's used.
  • Champion Lance has 6 Pokemon which ALL know the super-powerful Hyper Beam. His team consists of 3 under-leveled Dragonite, one of which has Outrage, which will easily take out most of your team unless you happen to have a then-rare steel type (only 5 fully-evolved steel Pokemon existed in Generation 2). They also know Thunder Wave, so chances are you'll be the slower one. His Aerodactyl is super-fast and has the flinch-inducing Rock Slide, which Aerodactyl ISN'T EVEN SUPPOSED TO LEARN in Gen2. Gyarados and Charizard will be the least of your troubles, but even they are quite annoying. In the remakes, he gets even harder. All of his Pokemon except for the higher-level Dragonite have flinching moves (Dragon Rush, Rock Slide/Thunder Fang, Air Slash, and Waterfall), and he isn't as prone to abusing Hyper Beam like he did before due to the requirement of a recharge, and the other moves on his Pokemon are so strong he doesn't need to anyway.
  • Jasmine in GSC/HGSS has two Magnemite and a Steelix, both of whom have rather high levels for that stage in the game. It doesn't help that Steel has a load of resistances, making her a tricky battle. However, if you picked Cyndaquil as your starter, this battle will actually be fairly easy. If you do some Sequence Breaking and head over to Mahogany Town first and dispose of Team Rocket there, you can gain plenty of experience points for your team, which will make facing Jasmine that much easier.
  • Chuck uses many variations of the Focus Punch strategies (some that are used by many competitive battlers) to make him terrifying. His horrifying Primeape in HG/SS will spam Double Team, then Focus Punch you to death. It can also use Rock Slide to deal with Flying-types, and it's pretty fast as well. There's also his Poliwrath, which can put your Pokemon to sleep with Hypnosis and follow up with Focus Punch. It can also hit hard with Surf, which gets a STAB, and Body Slam, which can potentially paralyze you.
  • Blaine in HeartGold/SoulSilver. All three of his Pokemon can hit incredibly hard with Overheat and use a White Herb to negate the status drop after the first use. His Magmar can also use Thunder Punch to deal with Water Pokemon, Sunny Day to further boost Fire-type attacks and weaken Water-type ones, and Confuse Ray to confuse opponents. Rapidash also knows Flare Blitz and Bounce, which also hit hard. Plus, Magmar and especially Rapidash are both pretty fast.
  • Blue in HeartGold/SoulSilver. Your team will be nerfed by Exeggutor's Trick Room, making the slowest Pokémon move first. The Mighty Glacier aspect of Pokémon like Machamp and Rhydon is thus conveniently removed, allowing them to destroy you. This is made even worse by the great type coverage provided by their extremely powerful move sets, and his Machamp has No Guard and knows Dynamic Punch. Of course, if you choose to rematch him, he turns out to have gotten a Tyranitar. Oh crap, indeed.
  • Bruno of the Elite Four in the remakes has a Machamp with No Guard, which allows it to still hit your mons even if you use a move like Fly or Dig. Just be thankful it uses Cross Chop instead of the universally-feared Dynamic Punch. It also knows Rock Slide to deal with Flying-types, Foresight to allow its Fighting-type moves to hit Ghost-types, and Revenge, which doubles in power if Machamp took damage that turn.
  • Koga has a Muk. If you cannot OHKO it, it will spam Minimize, and you'll have a tough time hitting it again. And even if you can hit it again, it holds Black Sludge, which restores health every turn. Similarly, his Crobat with Double Team. And most of his team can poison yours.

Generation III: Ruby, Sapphire and Emerald, plus Omega Ruby and Alpha Sapphire
  • Brawly is the second gym leader you face in the game, and this guy hits hard. In Ruby and Sapphire, his first Pokémon is a Machop that knows Leer to lower your defenses, Bulk Up to raise its Attack and Defense, as well as Karate Chop and Seismic Toss, two fairly strong moves at that point in the game, and the latter of which ignores type-effectiveness and defense. Then Brawly sends out his Makuhita: A rather bulky bruiser. In Emerald, his Makuhita knows the super-powerful Vital Throw, along with Reversal, which is a move that becomes stronger when Makuhita's HP is reduced. One of the main problems when battling him is the absurd jump in levels between the first gym and his gym, which is nearly right afterwards.
  • The rival battle with May/Brendan right before the third gym is stupidly difficult for some reason. At that point in the game your mons are around level twenty, so don't really have a variety of types in their attacks and most likely aren't fully evolved aside from some of the Com Mons you probably caught earlier, which won't do much good against a team consisting of Grass, Fire, and Water. No matter what starter you picked there is one Pokemon that's going to give you a hard time. Marshtomp's double weakness to Grass means that your rival's Grovyle can easily curb-stomp it, and heaven help you if their starter wasn't Treecko, because that Shroomish they get as a replacement knows Leech Seed and Mega Drain. In Emerald, they're even worse if you picked Treecko - if Combusken wasn't bad enough, you have to put up with a Wingull that knows Wing Attack. They also have a Lombre if you picked Torchic but it doesn't know any Water-type moves.
    • This fight got even worse in the remakes, especially for those who started with Treecko, since the rival's Combusken now knows Flame Charge, which raises its Speed every time it uses the move. Even one use of this will make it faster than everything catchable at this point, meaning even Pokemon with Super Effective moves will be forced to take a hit before they can attack. And it also has the ever-annoying Sand Attack.
  • Wattson, especially in Emerald. He uses four Pokémon, all of which know Shock Wave, an attack that NEVER misses. Plus, all of his Pokémon get STAB on it, essentially turning it into a Thunderbolt with perfect accuracy. His various Pokémon have moves like the sacrificial attack Selfdestruct (which still halves the target's defense in Gen 3); Rollout, which becomes more powerful after every successful hit; Thunder Wave to paralyze; and Sonicboom, which ignores type effectiveness and defense. To top it all off, his Voltorb is actually too low-level to learn Rollout or Selfdestruct in this generation, both of which it somehow has. In ORAS, the the Omnipresent move is now Volt Switch, (see Elsea below), on the other hand he has only three Pokemon this time and Voltorb no longer has Explosion or Self-Destruct.
  • Flannery. Her Torkoal is incredibly bulky, and hits incredibly hard with its signature move, Overheat. Even though it lowers its Special Attack stat when its used, in Emerald, she has it equipped with a White Herb which brings her stats right back to normal (only once, but that's really all she needs). A smart strategy would be to lower her stats beforehand, causing her to use up the White Herb immediately ...Too bad her ability White Smoke prevents this! She also knows Body Slam, which is not only powerful, but is likely to paralyze you (and this being the AI, it happens pretty much all the time). And to make this nightmare of a battle worse? She knows Attract, which makes it so male Pokémon are much less likely to attack her. It doesn't help that her other team members are likely to set up with moves like Light Screen and SUNNY DAY (which boosts fire moves and weakens water moves).
    • The remakes remove Attract from Torkoal's moveset but don't go celebrating because it gets replaced by Sunny Day to circumvent the Gen VI Nerf to weather moves. Also added is Curse to boost the already high defence even higher.
  • Norman. This guy is only the fifth gym leader, yet he has two Slaking, which have the highest attack stat of any non-legendary Pokémon up to then and a ton of HP. Even though they can only attack every other turn, they are still capable of KOing a Pokémon in one hit. He also has a Vigoroth, which is less powerful but pretty fast, able to attack before most other Pokémon you probably own, and isn't crippled by Truant. Finally, all three Pokémon come equipped with Facade, an attack that doubles in power if the user is poisoned, burned, or paralyzed. Norman in Emerald isn't too shabby either. He may have replaced one of his Slaking with Spinda and Linoone, but those two can certainly be annoying in their own way. Dear daddy sure meant it when he said he won't hold back even when he's up against his own child.
    • In the remakes, he trades Facade with Retaliate. While Status Effects are now safe to use against him, this presents a different problem. Remember Lenora's Watchog from Black and White? Well now, his Pokémon have it. If you knock out one of his Pokémon and he uses his other Slaking next, keep in mind it runs off a titanic base 160 Attack. Add that to a base 140 attack that gets STAB, guaranteeing a One-Hit Kill. And just like Lenora before him, all of Norman's Pokémon know this move now, so forcing him to switch with a move like Roar won't do any good.
  • Winona is basically the Whitney of Gen 3, having a fairly easy team up until the final round. Winona uses Flying-types, and her last Pokemon is an Altaria which knows the deadly combo of Earthquake and Dragon Dance, which she can't learn at the level you fight her, setting her up perfectly to sweep your entire team with powered up Earthquake and STAB Aerial Ace techniques, the latter of which never misses. Plus, Altaria is part Dragon-type, neutralizing its weakness to Electric-type moves. She's also the first leader to use Full Restores, which restore health AND cure ailments.
    • There's good and bad news in the remakes for her Altaria. The good news is that her Altaria no longer learns Dragon Dance and Aerial Ace. The bad news is that it now gains Cotton Guard and Roost. Cotton Guard raises physical defense by three stages. Roost is no slouch either, as it recovers 50% of its maximum HP. Don't have a special attacker for this fight? You're in a lot of trouble unless you pick up Toxic.
  • Tate and Liza in Emerald. It's fought in a Double Battle, a brand-new mechanic not seen much prior to this fight, which requires much more strategy than Single Battles. In Ruby and Sapphire, their team only consisted of two Pokémon (meaning you could, in theory, defeat them in one hit). These two Pokemon, incidentally, have a much stronger physical defense than most of the Psychic types you are used to fighting. This time around, however... You first need to fight through a Xatu (which can either use Confuse Ray on your fighters or Calm Mind to jack up its stats, aside from flat-out attacking with Psychic) and a Claydol, which spams Earthquake and AncientPower. The best part? Earthquake hits everything on the field, but thanks to their team choices, you're the only one who will get hit by it. Then there's Solrock and Lunatone you have to deal with. Solrock will use Sunny Day to power up its Flamethrower and instantly use SolarBeam, as well as attacking with Psychic, while Lunatone will put up Light Screen (Claydol knows it, too) to raise the opposing team's already high Special Defense, put you to sleep with Hypnosis, and do the same Calm Mind/Psychic combo as Xatu. The team is also prone to using moves (such as the aforementioned Claydol's Earthquake) that hit both of your Pokémon at once, raising the stakes that much higher.
  • In the remakes, Primal Groudon and Kyogre are some of the most brutal forced legendary fights in the series. Both have new abilities that ensure their weather is ALWAYS active, and gain extra benefits too. Groudon's Desolate Land makes it immune to Water moves, otherwise its biggest weakness, while Kyogre's Primordial Sea makes it Origin Pulse hit so hard even Pokemon that resist it are going to take huge amounts of damage. Thought you could use Grass types against Primal Kyogre? It has Ice Beam to cover them. Both also carry methods of restoring HP, Kyogre has gradual HP regain with Aqua Ring, while Groudon has Rest, which not only fully heals it but also gets rid of any status it might have had. On top of all this, unlike the mascot legendaries of Black and White and X and Y, Groudon and Kyogre have the minumim possible catch rate, meaning that even with all the odds stacked in your favor (1 HP, Asleep or Paralyzed, using the best kind of Pokeball for the job) they'll still only have around a 10% chance of being caught per ball. And considering every failed ball results in taking another hit from one of the strongest Pokemon in existance... players who want to save their Master Ball for the many postgame legendaries are in for a very tough time.
  • Sootopolis Gym is already hard enough with that godforsaken puzzle, and then in Emerald, there's Wallace's replacement and former tutor Juan. He starts out with his Luvdisc, which has a lot of Speed and loves to spam confusion (and Attract if your Pokémon is male) - terrible stats apart from Speed don't matter much when your Pokémon is busily damaging itself. And that's just the starting point - his other Pokémon will be quite happy to use Rain Dance, boosting the power of their Water moves to ridiculous levels (and as an added bonus, doubling the speed of any his Pokémon with "Swift Swim"). Whiscash hits hard with STAB Earthquake and has high HP, and his Sealeo is all too happy to annoy you with the seldom seen but incredibly nasty Encore. Of course, all of this pales in comparison to his trump card: Kingdra. Not only does it have excellent defensive typing, it has the ability Swift Swim, meaning that while it's raining, outspeeding it is nigh impossible, and that's on top of the rain boosting its power. It also uses the obnoxious Chesto-Rest strategy, allowing it to fully heal its HP and remove status at no cost (only once, but of course after that, Juan is all too happy to use Max Potions when its HP gets low). Did we mention Kingdra also has Double Team? Have fun with that.
  • Glacia wasn't too bad in the original games, but she became far more irritating in the remakes thanks to the Hail weather effect getting a slight revamp that her team (Four of whom know said dreaded move) can exploit to their best ability. Her wimpy Sealeos have been replaced with Froslasses, and they both get an evasiveness boost while Hail falls which makes them irritatingly hard to hit. One of them is particularly dangerous thanks to being able to trip your Pokemon up with Confuse Ray, and runs a constant risk of boosting all her stats with Ominous Wind. And her ace of a Walrein is an absolute behemoth of a Pokemon who can tank hits like they're nothing and give as good as she gets, and if any of your Pokemon are of a lower level than her, then they run the risk of being instantly knocked out with her dreaded Sheer Cold attack. And Walrein as well as Glacia's Froslasses know Blizzard, a powerful move which normally has shaky accuracy, but Hail removes that penalty meaning that they can constantly nail you with it for heavy damage.
  • You were led to believe Steven only trained Steel types, but you were led wrong! His very first Pokémon, a Skarmory, has Spikes, which deals damage to any Pokémon you switch in (provided they aren't airborne). It also has Toxic, a Poison-type move that gets worse each turn. To make matters worse, his Claydol knows Light Screen and Reflect, which increases the already high defense of all his Pokémon even more. He also has a Cradily who has excellent typing as well as great bulk with great type coverage (Giga Drain, Ancient Power, and Confuse Ray). On top of that, his ace is Metagross, a Steel/Psychic Pokemon with great type coverage (Meteor Mash, Psychic, and Earthquake).

    The remakes seriously ramp up the challenge. Steven's team's movesets have significantly improved. His Skarmory and Aggron's Sturdy Abilities have been buffed so you'll take at least two turns to take them out. Aggron's moveset is altered to be entirely physical rather than three special moves and one physical, and they're even stronger moves like Earthquake, Iron Tail, and Dragon Claw. But they're simple compared to his Metagross. Rather, Mega Metagross. It has an entirely physical moveset, hits like a train thanks to its Tough Claws Ability, which makes all its contact-based attacks even more powerful, and it's incredibly fast too. Even if your Pokémon can outspeed it, Metagross can still slam them with Bullet Punch. Do not take him lightly.
  • Archie´s team in the final battle against him in Alpha Sapphire is nothing to write home about, at least until he unleashes his Mega Sharpedo which may be a little fragile, but it is incredibly fast and powerful, and will tear your team apart if you are too underleveled.
  • It's not just the Gym Leaders: In the remakes, Contests are back and harder than ever, with many opponents more than capable of wrecking your chances of getting that elusive Ribbon.
    • For the Master Rank Tough Contests, there's Aiden and his Dusclops, nicknamed Topclops. It'll tear you down with Spite, chipping away at your hearts (and your chance of winning the Contest), and Curse, ensuring that it goes last so that it can Spite you in the next round.
    • Master Rank Cool has Clayton and his Heracross, Heracles. It always uses its move last in the first round to get max hearts with Reversal (a move that works best if used last, and earns 3 extra hearts if used after Endure), and then Endure to move back in line to pull off the Reversal combo again. God help you if he uses it while the excitement meter is at four stars. And in the last round, he'll use Giga Impact, which badly startles (-4 hearts) all the Pokémon in front. Hope you were lucky enough to go after him. Oh, wait. That's what Endure is for. Sucks to be you.
    • If these trainers are ever joined by Yoko and her Gyarados, Gyalaxy, and you don't have a move to make yourself immune to damage (Fly, Rest, etc.) you should just reset now and save yourself the pain, especially if all three of them are your opponents. It will use Dragon Dance to get itself a star and extra bonus points, Crunch to do massive damage to the previous contestant, Thrash which gets it massive points in exchange for being twice as vulnerable to jamming moves, and has access to Hyper Beam which works just like Giga Impact and it will use for its final move which startles all of the Pokemon before it. If you're first in the last round, you're essentially screwed as without a defensive move, you'll get hit by Spite, Giga Impact, and Hyper Beam, for about 10+ hearts worth of damage which can negate a Mega Evolution special move at max power and then some.
    • Master Rank Clever has Ruslan and his Kirlia, Lia. It uses Calm Mind to pump itself up to gain a star, which gives it a bonus for all of its moves, and then proceeds to use Stored Power which gives it triple times base points if it has a star, and then will use Psych Up which gains triple times the base points if it used after another Clever move was used. To top it all off, it's last move is Trick Room which shuffles the order of the contestants in the following round which can completely destroy your strategy depending on where you end up.
    • Master Rank Beauty has Layla and her Gorebyss, Gorflir, with a combination of Agility, which makes her go first in the next round, and Whirlpool, which jams the excitement meter and stops it from filling up for that round. Very annoying.
      • In the same category, Chaz and his Machoke, Macherie, come equipped with Return and Round for max hearts, Attract to make other Pokémon (including you, if the Random Number God decides you need a kick in the pants) nervous and unable to move, and Sunny Day for when the meter is at four stars, snatching the Spectacular Talent.
    • Master Rank Cute has Hailey and her Luvdisc, Lovelynn. Think it can't beat you because it hasn't got any insta-high-appeal moves? It'll use Psych Up and Draining Kiss to steal yours instead!
    • And, of course, there's Lisia and her Altaria, Ali, who has a chance of showing up in any Master Rank Contest once you've beaten them all, and is more than capable of whooping your ass. Master Rank Cute? She'll use Sing and unnerve your Pokémon, costing you precious hearts. Master Rank Cool? Outrage, Aerial Ace and Tailwind (especially the last two if used consecutively) will knock you flat. Master Rank Beauty? Dazzling Gleam and Round will earn it all the hearts it needs. Did we mention it can Mega Evolve, which means if it fills the excitement meter, it gets three extra hearts?

Generation IV: Diamond, Pearl and Platinum
  • If you chose Piplup, good luck defeating the Withdraw spamming Turtwig in the first rival battle.
  • Fantina. Her Pokémon have powerful Psychic-types moves that can easily mess you up pretty badly. In Platinum, her first two Pokémon are pretty easy, but her Mismagius can easily wipe you out. It has great stats for that section of the game and a great moveset to take advantage of them. It can use Confuse Ray and hit hard with Psybeam, STAB Shadow Ball, and Magical Leaf, which never misses.
  • Candice in Platinum. Most of her Pokémon are pretty easy, but after Abomasnow sets up some permanent hail with Snow Warning and Froslass comes out, things can get hectic. Endless hail will be chipping away at your health while an absurdly fast Froslass spams perfectly accurate Blizzards. Furthermore, its ability Snow Cloak will cause you to miss 20% of the time. Even worse, it can use Double-Team to even further decrease your chances of hitting it. Type advantages are meaningless if you keep missing while Hail and powerful coverage moves takes large chunks out of your HP every turn.
    • One easy way to defeat her Froslass is to bring a Sneasel that knows Faint Attack. Sneasel will likely be faster than Froslass and not only is Faint Attack a super-effective STAB move, it also never misses, ruining Froslass's evasion strategy. In addition, Sneasel's typing makes it immune to the hail and either resistant or outright immune to every attack Froslass can throw at it.
  • Volkner in Platinum. Most of his Pokemon are very fast and likely to strike first, and all of them hit hard. Most of them are also perfectly capable of dealing with type disadvantages. Raichu and Electivire can hit Grass-types hard with Signal Beam and Fire Punch, respectively. Luxray can use Fire Fang to deal with Grass-types, as well as Ice Fang, which is super-effective against everything that resists Electric-type moves.
  • Cyrus's battle in Spear Pillarnote  / Distortion World note . Gyarados used Aqua Tail / Waterfall! Bam, you're dead. Reload. Gyarados used Earthquake! Bam, you're dead. Gyarados used Ice Fang! Bam, you're dead. His Crobat is just as bad. Confuse Ray to throw you in for a loop, Air Slash to flinch, which is likely to happen, and Toxic just to make it more painful. Honchkrow has a good mix of attacks, especially in Platinum. Houndoom in the Platinum version can pack quite a punch with Flamethrower and Dark Pulse, as well as Thunder Fang in case you were trying to use a Water-Type against it. Weavile, Cyrus's strongest Pokémon, has very high Attack and Speed. He will be able to demolish your team quite easily thanks to its high coverage, with attacks like Night Slash, Ice Punch, X-Scissor, and depending on the version, Brick Break (Diamond / Pearl) or Fake Out (Platinum). His team's movesets are much better than what you have faced up to that point as well, so... less to be said, Cyrus's team is quite the thing for that point in the game. If you lose, you're climbing back up Mt. Coronet and through the Distortion World.
  • Hell, speaking of Team Galactic, Commanders Mars and Jupiter, due to the Early Game Hell aspect in Diamond, Pearl, and Platinum being downright absurd, with their level curves resulting in extensive grinding for the average player. Not only this, but they have also earned the bane of many for their hideously underleveled Pokemon, ranging from PURUGLY AT LEVEL 16 AND A SKUNTANK AT LEVEL 23, both with endgame stats and movesets that otherwise annihilate any player that dares fight them unprepared or worse, (And more than likely) underleveled. It doesn't help that these Pokémon have typing that leaves them each with only one type weakness. Purugly also knows the aptly-named Faint Attack, which can KO at low levels.
    • The double battle between them at Sky Pillar has you dealing with all the things that made their signature mon's difficult at the same time. Your rival is supposed to be helping you but he always stats with a Munchlax which can give you a bad start.
  • Flint. His Infernape is outright terrifying due to its high level and great coverage (Flare Blitz, Thunder Punch, Mach Punch, and Earthquake). He usually starts off with Sunny Day, and then the "fun" really begins. His Infernape's Flare Blitz combined with Sunny Day will pretty much instantly defeat anything and even then he still knows Earthquake. He's no slouch in Platinum either. If his Houndoom or Rapidash manage to use Sunny Day, you're in trouble. Rapidash is pretty damn fast. His strongest Pokemon, Magmortar, will hit extremely hard with any of its moves, and it can easily cover its type weaknesses. If Sunny Day is still in effect from one of Flint's previous Pokemon, Magmortar's Solar Beam will take no time to charge up, and it is super-effective against anything that normally has an advantage over Fire-types. It also knows Thunderbolt, which can make short work of most Water-type opponents and takes no time to charge up, in case Sunny Day is not active.
  • And then there's Lucian, who directly follows Flint in the Elite 4. He's a Psychic-type user, and his team is nasty. Mr. Mime using Reflect and Light Screen will stop your one-shots. There's also Alakazam, with huge Speed and Special Attack (plus Focus Blast for your Dark-types), and then there's his Bronzong. It knows the notorious Calm Mind + Psychic combo and Gyro Ball to take advantage of its low Speed. In addition, Bronzong has Levitate, meaning your Ground-types won't help you, so its only weakness is Fire. Oh, and it can throw Earthquake at you too. It doesn't help that your have TWO Fire-type options within Diamond/Pearl...and one of them, Infernape, is weak to Psychic attacks.
  • The champion battle with Cynthia is by far one of the most difficult fights of the franchise. Her team is very high-level even compared to the battle immediately before her, has varied types, and boasts perfect IVs across the board, meaning that they're far stronger than normal Pokémon you might fight at the same level. She has Spiritomb, which back then had no weaknesses to any types by defaultnote ; you just have to have a Pokemon strong enough to hit it until it gets knocked out. She has Milotic with Ice Beam for your Grass-types and Mirror Coat for your special attackers. And then there's her Garchomp, a Lightning Bruiser of a pokemon with powerful moves.

Generation V: Black and White and Black 2 and White 2
  • Gen V follows the tradition of Normal-type Gym Leaders being That One Boss with Lenora. Her Watchog knows Retaliate, a Normal-type move with a very respectable base power of 70. However, if a Pokémon in the user's party faints on the same turn, it doubles to a whopping 140, and that's not even counting STAB. Since Watchog will always be Lenora's second Pokémon, it can Retaliate right after you defeat Herdier, and it can OHKO pretty much anything you throw at it. It doesn't stop there, either. Her Watchog knows Crunch, a very powerful move at that point in the game, and can put your Pokémon to sleep with Hypnosis. Herdier is no pushover either, having stats comparable to Watchog's and knowing Take Down, which hurts a lot coming from a Normal-type. It also has Retaliate, if you feel like using Roar to take out Watchog first.
  • Likewise, Black and White 2 gives us the first Gym Leader, Cheren. All his Pokemon know Work Up, and while his Patrat isn't that big a deal, his Lillipup is. It'll probably be faster than you, and if it sets up Work Up, there's little you can do once it uses it once or twice, and it'll probably sweep your team. And in Challenge Mode he has a Pidove whose only attack is Quick Attack, and paralyzing that won't do you much good.
  • We also have the fourth Gym Leader, Elesa. She uses two Emolga (Electric/Flying) and a Zebstrika (Electric). Her two Emolga are very fast and know Double Team, and can potentially paralyze you with Static if your attack makes direct contact. Then her Zebstrika is so fast and so strong it mows down anything that comes in its path. And all three get Volt Switch, which does reasonable damage and switches them out.
    • She deserves a special mention, because unlike most other main game examples, there are very few, if any, surefire and feasible options available to you at this stage. Emolga is immune against Ground-type attacks, and it and Zebstrika have a super-effective move against Grass-types (Emolga knows Aerial Ace, which gets a STAB and never misses, and Zebstrika knows Flame Charge, which boosts its already incredible speed). Which calls for a Rock-type move, except that the available Pokemon that can land super-effective moves are full of issues. They are either slow, have low defense stats, shallow movepools, accuracy issues, and/or have defensive type weakesses against Elesa. Over-levelling is not necessarily a feasible option either due to the tendency of wild Pokemon in Route 4 being not very easy to defeat, and despite this, paying little experience points to overlevelled Pokemon (even if by just a couple of levels).
  • Elesa even has the dubious honor of coming after another That One Boss: N. Or more specifically, his Sigilyph, which has insane stats for that section of the game - its Speed is high enough to nearly guarantee it the first strike against anything you throw at it, and it knows Tailwind to eliminate the "nearly". Its Special Attack is high enough to virtually guarantee a One-Hit Kill on pretty much any Pokémon. Think it's a Glass Cannon? Not at that point in the game it isn't. It also has Magic Guard.
  • Even within the Elite Four, Marshal can be pretty difficult, because all his Fighting-types have very high Attack and wide coverage. His Sawk has Sturdy, which keeps you from OHKOing it. Throh and Conkeldurr have big HP and will likely not be taken down without you receiving a big hit in return, and in the rematch, he has a Breloom with Spore (Black/White) or a Lucario and Medicham (Black 2/White 2), the former of which has high Special Attack, especially for a Fighting-type; and the latter of which has a devastatingly strong STAB Hi Jump Kick and the elemental punches. If you're about to die, Lucario will slam you with ExtremeSpeed. And on Challenge Mode, that Medicham is replaced with a Machamp that uses No Guard with Stone Edge and Dynamic Punch, the latter of which always confuses you. He's not a foe you want to mess around against.
  • Shauntal can be a pain considering most of her Pokémon have a secondary type, meaning that they're actually somewhat well-balanced in comparison to other Elite Four members. They also have high defenses (Cofagrigus and Jellicent/Drifblim), high power (Golurk and Chandelure, which have the highest physical and special attack stats of all Ghost-types, respectively), or are just plain fast (Froslass and Mismagius). Also, her Mismagius knows Perish Song. Be glad it doesn't know Mean Look. Challenge Mode gives her a Gengar instead of Mismagius, which is fast and can hit very hard with STAB Shadow Ball and Sludge Bomb. In that same vein, in both the initial battle and rematches, Chandelure gets a Choice Scarf, which boosts its Speed by 50% in exchange for locking it into the first move it uses until it switches out or dies, so if you're not high leveled it's almost guaranteed to get a hit off.
  • The champion Alder, is easily one of the toughest, if not the outright toughest of the champions. You see, unlike most champions who like to stick to a certain type, and have a team with similar weaknesses you can exploit, Alder is the complete opposite. He has a very balanced team that combines offense (Bouffalant and Druddigon), defense (Vanilluxe and Excavalier), and speed (Accelgor and Volcarona). These Pokemon all have very good movesets with great coverage and they're all at very high levels (mid to late 70's) which is tough even by Champion standards, and is made all the more difficult that level grinding is especially hard in this generation.
    • The reason why he's so hard is not only that but his Volcarona is a monster. It has Quiver Dance, Hyper Beam, Overheat and Bug Buzz. If it gets off 2 Quiver Dances it is capable of destroying all non Rock Types. If you have a Rock type or Water type this battle is pretty easy because while it's Monotype a lot of his Pokemon are Bug types but that Volcarona is a problem if you don't have a Rock type with it's Hyper Beam and Overheat.
  • If your Pokémon happen to be kinda slow, Clay's Excadrill will likely wipe out your entire team. Made worse by the use of Hone Claws which increases Attack and Accuracy.
  • The Final Boss, Ghetsis, can be a real hair-puller, coming immediately after another difficult fight without so much as a chance to save — thankfully your Pokémon are fully healed between the fights, but this is still a trick the franchise rarely pulls. Some of his Pokémon are more deadly than others; he starts out with Cofagrigus, which will badly poison you with Toxic and stall out your Pokemon with a combination of Protect and its excellent defenses. It can also override your Pokemon's ability with Mummy if you use a move that makes direct contact. Bouffalant can rip through whole teams with a powerful STAB move powered up even further by Reckless and has amazing defenses. Eelektross is an Electric Pokémon with Levitate (which means no weaknesses) and has the offensive stats and type coverage to do more than stall. But all that's just preparing you for his worst: an underleveled Hydreigon. This thing is monstrous. Aside from the fact that it's almost certainly a couple levels above you, it has astonishingly good type coverage and perfect EVs and IVs. Make no mistake: if you don't bring a crapton of Revives and Hyper Potions, you will lose.

    In the sequels he doesn't let up much. His Cofagrigus has high Defense and will use Protect to guard and Toxic to wear down your team, and also can override your Ability with Mummy when hit by a move that makes direct contact. His Toxicroak also is very strong and has an Action Initiative move in Sucker Punch. Drapion has high Attack and its Night Slash attack makes good use of its Sniper ability, plus it's decently bulky and very fast. The Eelektross is just about the same as it was before, though it's got Thunderbolt instead of Wild Charge. And the Hydreigon? It's at a lower level (52, 56 in Challenge Mode) than before, but thankfully uses a less versatile, physical-oriented moveset (Dragon Rush, Crunch, Rock Slide, and Frustration).
  • Black 2 and White 2 throw a pretty hard boss at you in the Plasma Frigate, in the form of Colress. His first Pokémon is a Magneton. It has Sturdy, so you can't OHKO it and it will proceed to Thunder Wave you. To add on to that, it holds the Eviolite, which boosts its Defenses by 50%, so it's bulky, too. Next up, it uses Volt Switch to get out of there while hitting you rather hard. His Magnezone has Sturdy and Thunder Wave too, so beware that. He also has a Beheeyem with Calm Mind that can boost up and hit you pretty hard, a Metang with powerful moves, including Rock Slide for your Fire-types, and a Klinklang that boosts up with Shift Gear. He even poses a bigger challenge than the team Ghetsis uses in a later fight.
  • For the Champion, Iris is quite a bit more difficult than the previous Champion. The first Pokemon you're up against is another underleveled Hydreigon. It will plow through your team with Dragon Pulses, Surfs and Flamethrowers, which hit everything in the game for at least neutral damage.note  Then, once you get through that, you'll have to fight through an Archeops, which is fast and hard-hitting; Lapras, which has high HP and defense and knows Sing; Druddigon and Aggron, who are just tanky in general; and then Haxorus, which has a ton of powerful moves and Mold Breaker. It can use Dragon Dance to boost its Attack and Speed, setting it up to sweep your team, and you can't even OHKO it because it's holding a Focus Sash. note 

    And Arceus help you if you're playing on Challenge Mode, because her team gets a complete redesign. Each of her Pokemon gets at least one of their moves replaced with a more damaging alternative and get held items that either boost the power of their moves or accuracy. But the most dangerous change is Druddigon being replaced with a Salamence holding a Life Orb.

Generation VI: X and Y
  • Siebold. More specifically, his Gyarados. Even more specifically, the fact that it knows Dragon Dance. It will easily achieve a Total Party Kill. It also has good coverage for its weaknesses: Earthquake for Electric-Types and Ice Fang for Grass-Types. The rest of his team is no slouch either: Clawitzer has very wide coverage and all of its moves are boosted by Mega Launcher, Starmie is extremely fast and packs Dazzling Gleam for any Dark-types (and Dragons) that would try beating it, and Barbaracle is a powerful physical attacker with amazing coverage.
  • Grant is difficult for many players. He uses the two Kalos fossil Pokémon, Amaura and Tyrunt. Amaura can hit you with Rock Tomb, which slows you down, and can paralyze you with Thunder Wave. It also hits incredibly hard with Take Down, which turns into an Ice-type move thanks to its ability Refrigerate, as well as Aurora Beam, both of which are a good way to deal with Grass-types. His Tyrunt also knows Rock Tomb, as well as Bite and Stomp, two moves that can make you flinch and the former of which is boosted by its Strong Jaw ability. It's also part Dragon-type, neutralizing those Water and Grass weaknesses you were hoping to exploit. And both Pokémon are very bulky for this point in the game, so even super-effective moves won't take them down easily. Adding to this is that he addressed his type disadvantages at an earlier stage than what would usually be the case in most previous installments, so it's quite easy to get caught off-guard.
  • Clemont can also be tough for those who think they can rely on type advantages. His start-up, Emolga, can completely evade Ground types and hit Grass-types hard with Aerial Ace, use Volt Switch to evade and switch-out, and paralyze you if you use contact moves due to its Static ability. Heliolisk knows Grass Knot to counter any Ground-type Pokemon you will bring up. Magneton also knows a STAB special Steel-type attack which can hit decently and also lower your accuracy, and has the ever so annoying Sturdy ability. And Magneton and Heliolisk both hit hard with Thunderbolt. In short, you can't just rely on type advantages alone; you will need to be able to strike first, which is not easy to do considering how fast Emolga and Heliolisk are, and effectively exploit any stat weaknesses Clemont's Pokemon have.
  • Xerosic is a minor case of this. His Crobat is extremely fast and has a decent mix of attacks, including Air Slash to possibly make you flinch and Cross Poison for a heightened critical hit ratio (both of which are STAB moves, by the way). After that, his Malamar has Contrary + Superpower, plus Retaliate for double the damage right after you knock out his Crobat.
  • The final battle against Lysandre may be one of the toughest villainous team leaders yet, having strong Pokemon at very high levels for the point in the game you encounter him. Of course, this isn't helped by him also using Gyarados, or rather Mega Gyarados, which wields a variety of powerful attacks with insane type coverage.
    • Subverted in Pokémon X, where the player has the option to transfer the Fairy-type Xerneas to their party before battling him. Xerneas has the type advantage and stats to One-Hit Kill most of his Pokémon.
    • Double Subverted however in that Gyarados knows Iron Head to deal with its new Fairy weakness.
  • Most of the above problems become non-existent if the player chooses to make use of the Exp. Share that they get fairly early on in the game - experience is given a lot more freely in Kalos, and it becomes rather easy to become That One Boss to enemy trainers, yourself.
  • For the Super Training Mini-Game, the special attack boosting Magnezone often trips up new players. Its targets constantly move in a circular pattern, and unlike similarly mobile enemies, it fires waves of homing projectiles that force the player to maneuver and readjust aim.

Pokemon Puzzle League
  • Team Rocket of all opponents, is easily one of the toughest opponents you'll face. Right before you try to gain the Earth Badge from defeating Giovanni, Jessie, James, and Meowth ambush you and force you to face them first. Ironically as opposed to most games where they're defeated easily, in this game they are a major threat and know how to chain combos like nobody's business as they can easily hit a 10+ combo even on lower difficulties which is usually enough for an instant victory, and they're even worse on harder modes. The Giovanni battle right afterwards while formidable is nowhere near as difficult as the previous battle.
    • The last boss, Gary, is incredibly difficult even for a final challenge, as he is quick and easily makes multiple chains for major damage on your side of the field before you can react. It gets even better when you defeat him on hard mode and you face the True Final Boss, Mewtwo, who is a much more difficult version of Gary. The best part about this whole ordeal is if you lose against the True Final Boss (which is very likely), you have to defeat Gary all over again.
    • The reward for defeating Hard Mode completely is accessing Very Hard Mode, where everyone hits this status. And then, if you beat that, you get access to Super Hard Mode, where everyone becomes an SNK Boss.
  • Butch and Cassidy in the Spa Service mode. Their level scrolls at 45, they have the rare diamond blocks to throw off basic combos and chains, and they have a very large health meter. They're even harder than Giovanni, the final boss, as while his stage features are mostly the same, his is in a 3D scrolling area that makes it easier to rack up combos and stop the scrolling. Butch and Cassidy's isn't. To make matters worse, you only get one shot to beat them; the only way to fight them more than once is to quit in the middle of the level or restart the mode.
  • The final Team Rocket levels in Spa Service will often have a very high scroll rate and start very close to the top, and take a long time to complete.

Pokemon Ranger
  • Charizard in the first game. The second time with him is a lot harder. Not only does he like to fly around while blowing flames, but his fireballs scatter much more densely, making it hard to circle him — and even with assists, it takes a lot of loops to get him. It also doesn't help that if you take too long, he flees the battle and you have to start all over again...
  • Several players have a pretty rough time with Steelix, too. Even when he coils up (which is about the only time that circling him is even possible), his sheer size makes drawing those loops awkward. Having multiple Water and/or Fighting assists comes highly recommended.
  • Drapion is a rather irritating boss due to the fact that you face two group captures directly before it. And that you come to a full stop at one part unless you happen to have a Normal-type Poké Assist ready.
  • Flygon. You're not allowed any other Pokémon because it's a "test" and the bloody thing resists Plusle/Minun's assists. And it's incredibly fast, making it nigh-impossible to get the amount of circles you need to finish the battle.
  • Entei. Not only is it fought at the apex of a Sequential Boss gauntlet of all three legendary beasts, you have to deal with the fact that it basically attacks the entire screen. And in the refight, you can only bring three Pokémon for the whole thing...
  • Metagross can be a real pain if you don't have the right assists. It pretty much fills the screen with beams and makes shields for itself.
  • Regigigas in the second and third games causes damage just by WALKING. It's easy to screw up and lose and assisting Pokémon, and your Styler gets damaged if you don't circle the thing immediately before or after it launches an attack.
  • Ditto in Guardian Signs. You thought fighting each of the beasts individually was bad, this thing will transform into each of them over the course of the fight. Unless you have a variety of Poké Assists, you're in for a long fight.
  • Feraligatr in the third game. It's not so bad before and after it rages, but while it's raging, it tackles all. the. time. And 9 times out of 10, it will charge off screen so you can't circle it between attacks, not that there's much time in between for circling it. And each tackle does 10 points of damage.
  • Salamence in the first game. Like with Flygon, you aren't allowed to have other Pokémon with you. Unlike Flygon, however, it's slow but more than makes up for it by having to draw a ridiculous amount of circles around it (22, surprassed only by three Pokémonnote ). It also outright ignores your starter's assist. When on ground, circling him is difficult, as it shoots beam around, likely hitting your Capture Line. The only reasonable time to circle the guy is when he's flying, and even then he can interrupt. Also, simply landing counts as an attack, and it hurts.

Pokémon Colosseum
  • The Cipher Admins are all That One Boss, not because they were difficult to defeat but because you had to spend ages trying to capture the legendary beasts while keeping yours alive. Don't forget the fact that, when you catch a Shadow Pokémon, all they have is Shadow Rush (at least in Colosseum, anyway)... but before you catch them, their original trainers can use all of their other moves. Hence allowing the aforementioned Thunderdance combo. It also means that there's a chance that your Shadow Pokémon-owning opponent could use Shadow Rush, which gives recoil damage. This means that someone trying to catch a Shadow Pokémon had to be very careful about the opponent's HP; leaving it at 1 HP or near it could leave it vulnerable to its own recoil. At least the Shadow Pokémon owners generally didn't use Shadow Rush, but that doesn't mean the possibility was gone. Thankfully, XD eliminated recoil except on a couple moves.
    • Ein has a Raikou with a damaging Thunderdance combo. He's also a big fan of inflicting the Confusion status, and as is usual for the Pokémon games, your team will suddenly become about 250% more susceptible to the detrimental effects of Ein's status ailments. You hopefully have Suicune and Entei then, but his water team will destroy the Fire-type Entei, and Suicune falls easily to Raikou's Thunder.
    • With Dakim, you had to try to capture the legendary Fire Pokémon Entei, who was weak to Ground moves. Guess what Dakim's favorite move was? That's right, Earthquake! Every one of his Pokémon had it, and got STAB bonus from it as it hit everyone else on the field, which meant that if Entei came out too early, it was going to get knocked out before you could catch it. If their constant Earthquakes didn't defeat you, the high probability of Entei fainting too soon would probably have you replaying this fight over and over again.
    • Miror B. has several Ludicolo that use Rain Dance to activate their abilities Rain Dish and Swift Swim, meaning either they regenerate their health or make them far faster than you. They are all fully evolved Pokémon at a decent level and have very few weaknesses you can exploit at that point in the game. Fortunately, he's easier in the sequel, although he does have a Shadow Dragonite in the last battle.
  • The final boss, Evice, is pretty difficult, but generally par for the last boss of a Pokémon game. However, should his Slaking and Slowking end up on the field together at any point, you're screwed. Slaking's stats are equal to those of Groudon's. Slowking will use Skill Swap at the first possible chance, which gives it Truant and gives Slaking the ability to attack every turn. His other Pokémon generally have high attack stats, as well as moves that boost their strength to even higher levels. Special mention? His Scizor, who can Baton Pass Swords Dances if it isn't taken care of onto another one of his Pokémon; and his Salamence.
Pokémon XD: Gale of Darkness
  • Exol is also a really tough fight as he his Pokemon are in the low 20's which is high for this point and his team has very good type coverage. Namely his Raichu and Loudred. He also has attacks like Shock Wave which is extremely dangerous at this point as it doesn't miss and early on it's 60 base power is incredibly strong. His Raichu also gets Dig and Seismic Toss. The type coverage with his team and his high levels make this an extremely hard fight. His Shadow is easy however as it's Mawile before Mega Evolution existed.
    • The second fight with Snattle hurts quite a bit if you don't have the right number (or quality) of sweepers. Why? Starmie. It hits fast, hard, and if you haven't been dragging a tank of a Shadow Pokémon around to soak up the damage, it can wipe out an entire non-Shadow team. Its Shadow Solrock partner, by contrast, is almost insultingly easy after that thing.
    • And even when you win, Cipher Peon Kleef proves Dangerously Genre Savvy by ambushing your team as you go through the Door to Before, while the next healing machine is through him or another boss and the last one is a major backtrack. Thankfully Kleef is otherwise pathetic (a team of stallers with no Shadow Pokémon to snag) and XD allows saving anywhere, but it really hurts when your team has such major injuries.
    • Thug Zook, when encountered outside the Key Lair immediately after the Snag Machine is stolen, is a nightmare. He has a Shadow Zangoose with him that is above the typical level for that point in the game, and it will happily kill off one of your team members every single turn, first, without fail. Essentially this forces you to constantly pick away at it with the survivor, hoping you have enough firepower to kill it before it wipes out your whole team, and then proceed to spam Revives and healing items while his other Pokémon are busy trying to kill you less effectively. It's so bad that in the rematch with him, his mons haven't leveled up at all, and he's still a very hard opponent to beat.
    • Grand Master Greevil can be this for the unprepared. Three Shadow Legendary Pokémon (the legendary birds) at Lv. 50+, plus another three relatively strong Shadow Pokémon (Exeggutor, Tauros, Rhydon) at Lvl. 46+. What this means is that powerful attacks will be headed your way, and every attack against you will be super effective thanks to the Shadow type, as well as a low catch rate for the Legendary Pokémon. If you're not prepared, you'll run out of Revives and/or Snag Balls before all six can be snagged.
    • Before him, there's one of his right-hand men as well as the penultimate boss, Eldes. He has four Shadow Pokémon, which will be the highest amount you've seen in the game so far, and they are all hard hitters. Special mention goes to his Marowak, who hits extremely hard thanks to its held item the Thick Club, and his Salamence, who is Level 50 at a point where your past opponents have been in the mid forties. Without a decently bulky Shadow Pokémon to absorb their blows, Marowak and Salamence will pretty much one-shot anything you throw at them. And to make things worse, all of them (save for his Shadow Manectric) are decently bulky as well, making them even harder to take down. If it's any consolation, his non-Shadow Ninjask and Flygon are nowhere near as annoying to deal with as the rest of his party.
    • The other right-hand man, Ardos, is far more nasty in other ways. Half of his team consists of very dangerous shadow pokemon, and the other half, consists of very dangerous non-shadow pokemon, unlike the aforementioned Ninjask and Flygon. His signature Pokemon, Alakazam, which utterly one-shotted a previous entry, has all elemental punches and has a very powerful STAB attack, all coming off from one of the highest special attack stats in the series, and he can easily target many shadow pokemon's, and even regular pokemon's weaknesses. Heracross and Kingdra are no slouches either, the former has a powerful STAB megahorn attack which will leave a mark, the latter has a weakness to a type that you most likely won't have, and can cover that weakness easily. Two of his shadow pokemon are extremely fast, and have a nasty move called "Shadow Half" which works like an unholy combination of pain split and super fang, which halves the HP of every pokemon on the field, with a recharge turn. The third shadow pokemon is a Snorlax, which introduces the powerful Shadow End move, which will destroy non-shadows very easily, and works really well together with its equally dangerous teammates. In addition, the first two shadow pokemon have four different shadow moves, including Shadow Break, Shadow Storm, Shadow Sky, and Shadow Mist. Oh and the Snorlax has leftovers, which actually makes this one of the most annoying shadow Pokemon to catch, as every turn, the catch rate decreases.

Pokemon Mystery Dungeon series: Rescue Team and Explorers
  • Those bloody group bosses. I'm talking to you, Luxio/Electrike tribe, Dusknoir and Sableyes, 'The Grand Master of All Things Bad' and their cronies. And let's not forget Darkrai and pals.
  • Articuno in the first games. Its main attack is Powder Snow, which will hit both you and your partner and the damage is high enough to OHKO you. Not even Pokemon that resist Ice are safe from it, so unless you brought plenty of Reviver Seeds, this is a battle that pretty much rides on luck.
  • Primal Dialga is no pushover either. He packs a lot of HP. He's got a great defensive typing (Steel/Dragon). He's got the intimidator IQ skill, which more often than not prevents you from hitting him at melee range. And to top it off, he's got Roar of Time, which can hit both you and your partners from anywhere in the arena, is surprisingly accurate and deals triple digit damage (thankfully you can turn it into a double-edged sword via confusing it) a stage when you just reached triple digit HP, which means you'll really need those Oran Berries and Reviver Seeds. Oh, and did we mention that you fight in your unevolved forms and losing forces you to climb Temporal Tower again?
  • Darkrai. It's hard enough getting to him with Cresselia in tow, and he wouldn't be all that hard to beat, being considerably weaker than Dialga, were it not for the exact same Cresselia whose relatively annoying tendency to throw herself into battle with just about everything becomes a downright suicide attempt against Darkrai, to whom Cresselia has a weakness. No matter how hard you try to keep her safe behind yourself and your partner, she will simply move right next to Darkrai all over again, allowing Darkrai to destroy her in 3-4 turns, if you are lucky. And, of course, as soon as she goes down, you all teleport out. The only way to overcome this is to take out Darkrai before Cresselia can go down, which is quite difficult, or fill your bag with a lot of revive seeds.

Pokemon Mystery Dungeon: Gates to Infinity
  • The final battle with Munna and cronies is truly a difficult fight. Try to use a Wonder Orb to cripple the team? Not gonna work, they've got a Team Skill that'll wipe it immediately. It's also a seven-on-four battle. Munna herself will spam Hypnosis and Psybeam to inflict status ailments on you, and bulk up her defenses with Defense Curl (fortunately, Synchronoise, the other move she has, has no effect on anybody). Get put to sleep, and you're screwed; especially since you are closest to her. Toxicroak will spam annoying moves like Taunt and Swagger, Chandelure can confuse you (easily the most frustrating status ailment in the game), poison you, and hit you with Flame Burst, which deals an additional 10 damage to everyone in your party after hurting you. On top of that, the four Gigalith will spam Harden and Iron Defense to tank up their defenses, and may randomly survive fatal damage because of their Tough team skill. You will get stomped if you're not careful. Kyurem afterwards is almost a cakewalk compared to this.

Pokémon Super Mystery Dungeon
  • The fight with the Void Shadows at the end of Reverse Mountain. The two Mega Gengars aren't so bad beyond having Confuse Ray, and even the Mega Tyranitar isn't too hard, other than being very bulky. It's the Void Shadows themselves that will give the most trouble, as they can duplicate themselves, they have an area of effect attack, and they can also drain your health. Worse still, their attacks do not have types, so you cannot resist them. They also have about 225 HP apiece. If you don't take them out before any of the other enemies, you'll be overwhelmed very quickly.

Pokémon Conquest
  • During the initial story, Oichi warns you that Normal-types are weak to Fighting-types when attacking the Fighting kingdom Pugilis. It so happens you have to take your character and Oichi every time you attack a kingdom, and your two Pokémon are Eevee and Jigglypuff, neither of which you can possibly evolve at this point in the game yet. Right off the bat, two of your Pokémon are at a heavy disadvantage. And if you're new to the game and don't know the strategy for how to conquer Pugilisnote , you're going to probably going to end up having to just fight it out until the enemy is all defeated, which ain't easy.
  • Taking Nixstorm is very difficult to conquer in any storyline. It's the Ice-type kingdom, and the battlefield is a large mass of Frictionless Ice like you know from the main games, making it very difficult for Pokémon to move around. Not that the Nixstorm warlord Mitsuhide cares, his Lapras is an Ice-type, as likely are the Pokémon of his allies, and they can move on the ice normally. You'll need Flying-types or Levitate to move normally (and remember Flying is weak to Ice), because Ice-type Pokémon of your own to use are not easy to find at that point in the game. And Mitsuhide's Lapras is very powerful with a nasty Ice Beam that can really hurt anything it finds in that icefield, and Shell Armor to block critical hits. Finally, on top of it all, in any storyline where Mitsuhide remains in Nixstorm, including the initial storyline, one of his allies has a Munna with Hypnosis.

Pokemon Stadium: Now with its own page, but here are some examples below.
  • In the original Stadium's Pika Cup, the 7th opponent (second to last) you have to face is a Lass who bends the rules to her favor. The ruling states that the total level of the three Pokémon you use can't exceed 50. The computer, thus, gives you a choice of lvl 15 Pokémon (and you must use these if you can't connect your own Generation I game to the game, especially now since neither game will save due to the save battery in almost all copies by now being dead). Lass, however, has access to two lvl 20 Pokémon, a Gyarados and a Tentacruel. She's only able to use one, but she only needs one, as either could devastate your party. Her party is also well balanced and unpredictable. Pick Hitmonlee to face her Dewgong or Meowth? Surprise, she sends out Mr. Mime. Oh, and this is her in Round 1.
  • The original Stadium's Prime Cup had a Gambler for your second opponent who specialized in having all of his Pokemon spamming One-Hit KO moves, which back in the day had about a one in two chance of connecting. This means that he could use his Dragonite to Horn Drill or his Dugtrio to Fissure you for an instant defeat. His Pokemon is a good combination of attack, bulk, and speed which means he will usually go first and potentially sweep your team if he's fortunate essentially turning this match into a giant Luck-Based Mission. Also Arceus help you if you're going for the Surf Pikachu challenge which requires you to use a team of your own Pokemon that has Pikachu in it to complete all eight rounds of the second Prime Cup.
  • Stadium 2's Janine. She's easy in Round 1, but what's her strategy for Round 2? Baton Passing multiple layers of Double Team (a move normally banned in Smogon competitive play for being too luck-based). All her Baton Pass targets can take a few good hits, have Confuse Ray, Attract, or Swagger to screw with your chances of hitting even further, and will wear you down with Toxic and Sandstorm. If you're planning to just switch out, take note that she's also packing Spikes and Mean Look. She will slowly torture you to death unless you come prepared with Haze and Heal Bell, but even then you're still at the mercy of many elements of luck.
  • Erika had a really annoying rematch Vaporeon because of the former ruling that Sleep Talk could pick Rest again to restore the health. Vaporeon having a ton of HP and decent special defenses did not help matters at all.
  • The Elite Four fights in both Stadium games. They consist of a gauntlet of five fights in a row, each very hard thanks to a mix between genuine difficulty and cheating on the AI's part, and if you lose, you have to start all over again. Losing to Lance in Stadium 2 when you were so close to defeating him is common, and insanely frustrating. It's sightly easier if you import your own tailor-made team from one of the main games, but if you don't have one or can't, you're stuck with using rental Pokémon, which make the fights a hell of a lot harder.
  • Sashay from the "little cup" Sunny Park Colosseum in Battle Revolution. Especially her Treecko. That stupid thing spams Energy Ball like there's no tomorrow. A big attack like that on a little baby is a big surprise for those who aren't prepared!
  • Everyone becomes That One Boss on the "Level 50 — Rank 8" setting. The boss of the Colosseum will throw uber legendaries at you just to screw you over. "Colosseum Leader Taylor sent out KYOGRE!"—cue rage quit—And it's not just the bosses! On rank 8, everyone leading up to the boss will use 3 legendaries at the very least.
  • And don't even get started on Mysterial and his annoying Chansey! Kingler, Golbat, and the rest are bad enough, but that Chansey is Normal-Type and hard to take out.
  • The Sunset Colosseum boss. His team varies due to the nature of the round-you and your opponent both select rental Pokemon from a pool-, but he usually has a Vigoroth. It has good stats to begin with, and it loves to OHKO or severely damage as many as it can of your team with Body Slam or Brick Break. Plus, it's Normal-type and resists everything but Fighting moves. If you choose Machop, you have fighting moves, but Vigoroth always seems to move first and remove the option. Then he has Gabite. You can damage or eliminate it with your own Gabite or Gible, but he usually gets Dragon Rush off first, taking yours out. And if he has Luxio, one Ice Fang will also take Gabite and Gible out. Then there's his Grovyle, with Leaf Storm.

Pokémon Trozei!
  • In Pokemon Shuffle, a lot of the Mega Evolutions are tough. But the standout seems to be Stage 120, Mega Glalie. To start things off, you don't just have your four chosen Pokemon on the field; the Mega Glalie fight also has Glaceon drop in along with what you brought in! He will also change your Pokemon into Snorunt on occasion. Know the only type that Ice resists? That's right, Ice itself! The worst part, however, is when he freezes two columns solid at once! And it's likely where you would have made your next move. Now, it's possible for Mega Glalie to freeze the entire field, in which case the board is reset, and you're probably getting some damage in. If he keeps freezing the same two columns over and over, you're stuck with poor choices that won't do a lot of damage to Mega Glalie. It oftentimes takes a combination of purchasing five extra moves, a Disruption Delay, a Mega Start, and/or a Complexity -1 to defeat him. And you may even need five more moves at the end and have to spend a Jewel. Fortunately, you do get a Jewel in return if you defeat him.
  • People also have a load of trouble with Mega Gengar. Like the Mega Glalie battle, Mega Gengar throws in its own "support" Pokemon that isn't very effective against it, namely Eevee. And he loads the field up with them! Unlike the Mega Glalie fight, however, Mega Gengar only ever freezes the middle two columns, which is the absolute worst place to do this because it makes combos damn near impossible! He also turns your support Pokemon into Haunter. Three. Moves. In a row. Unsurprisingly, actually using Haunter only mitigates this problem a little.

Pokémon Rumble
  • If the Escort Mission "Restraunt Opening" was not hard enough, the Slurpuff battle in World can be this. Coming right after the Tarous midboss, Slurpuff has come prepared with a heckload of Swirlix, who endlessly spawn to no end and will gladly spam Attract, which can and will home in on you and make your Pokemon unable to do anything at all. In addition, it has a move that can restore its HP. You also have to do this mission and boss fight within the time limit, and if you either run out of time or if your Mii loses all of its HP, you have to do the mission again.

Isn't it a little odd how almost every Gym Leader is on this list? No, not really.

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