- Ambiguous Gender: Staraptor, Buizel, and Gible are all confirmed male, and both Torterra and Infernape are pretty implicitly male as well, but Gliscor is more debatable.
- Badass Crew: Notable more so than normal because unlike most of Ash's previous teams, most of his Pokémon on his Sinnoh team made it to their final stage, with the exception of Buizel and Gible.
- Put on a Bus: At the end of Diamond and Pearl they're all left at Oak's Lab while Ash heads to Unova.
Ash's Pokémon (Sinnoh Region)
- Voiced in Japanese by: Kiyotaka Furushima (Mukkuru and Mukubird), Katsuyuki Konishi (Mukuhawk)
Voiced in English by: Sarah Natochenny
Starly was caught by Ash moments after first arriving in Sinnoh where his Aipom accidentally bumped into it during a search for their lost Pikachu, which Ash decides to use Starly to help with the search. He later evolves into Staravia during a battle with Team Rocket, and then into Staraptor in order to win a PokéRinger competition.
Staraptor stayed on Ash's team throughout the Sinnoh journey, and remained one of Ash's top fighters. His defining characteristic is that Staraptor will perform a face-fault whenever he's shocked or confused by something.
- Bare-Fisted Monk: Knows Close Combat. And yes, it is weird to see a raptor punch and kick his opponent with his wings and talons.
- Blow You Away: He knows Whirlwind, which is a wind-based status move that he used it for offensive purpose. It's actually called Gust in the Japanese version.
- Call-Back: The episode where Staravia evolves into Staraptor mirrors that of his Hoenn equivalent (Taillow to Swellow).
- Corner of Woe: After getting sidelined for Ash's first gym match, Staravia goes sulking face-first against a pillar.
- Crash-Into Hello: Ash and Brock met Starly when Aipom crashed into him.
- Friendly Rivalry: According to Professor Oak, he and Swellow have formed one during their stay at his ranch, with the two of them often having aerial races with each other.
- Heroic BSoD: Has one when Ash doesn't choose him to fight Roark, complete with a Pokémon Speak Big "NO!".
- Noble Bird of Prey: The inspiration behind the Starly evolutionary line, and Ash's Staraptor is no exception, being one of his stronger Flying-Types.
- She's a Man in Japan: Is female in the Czech dub and Latin American Spanish dub.
Turtwig was met by Ash and company along the way to Jubilife City where it served as a forest protector for the Pokémon around Clara's home, going so far as to protect Pikachu from Team Rocket and Ash believing them both to be enemies. Turtwig soon realizes his mistake and apologizes, but also begins to bond with Ash after the two deal with Team Rocket. It then challenges Ash and Pikachu to a battle, which results in Turtwig's capture.
Along the Sinnoh journey, Turtwig evolves into Grotle during a battle with Paul, and then into Torterra during a battle against Team Rocket. Sadly, Torterra has become well-known amongst the fandom as the Pokémon amongst Ash's team that couldn't win any of its important battles after evolving.
- Big Brother Instinct: Similar to Bulbasaur in a way that he is protective of other Pokémon.
- Death-or-Glory Attack: Whenever he uses Rock Climb during a fight, the victor tends to be quickly determined after it either succeeds or fails.
- Demoted to Extra: Turtwig was Ash's main battler early on in Diamond & Pearl, being key to his victories over both Roark and Gardenia. Once Chimchar and Buizel joined Ash's team, Turtwig gradually faded into a background player, even after its two evolutions.
- Determinator: Grotle is left heartbroken when it loses its signature speed after evolving, but through dedication, it manages to teach itself Rock Climb to compensate.
- Fragile Speedster: As a Turtwig, he's pretty fast. Having to change fighting styles after evolving stymied it for a few episodes.
- Gentle Giant: Huge upon evolving into Torterra, but remains a pretty docile, friendly Pokémon just like when he was still a Turtwig.
- Mighty Glacier: After evolving into Grotle, and the Torterra, he gets stronger, but the extra weight and size cost him the speed he had as a Turtwig, which may also explain why Ash lost a lot with him, since he's more used to Lightning Bruiser Pokémon than Mighty Glacier ones.
- Overshadowed by Awesome: The biggest victim once Infernape became Ash's signature mon. At the start of the season, Turtwig was Ash's designated starter, having a Friendly Rivalry with Paul's Torterra, and even having its own arc of having to get used to being a Mighty Glacier after evolving. Then, when Chimchar joined the team, his significance got reduced. To make matters worse, Torterra was often used to show how much Ash's other Pokémon (Infernape and Gliscor) had grown.
- Pintsized Powerhouse: As a Turtwig, he was strong enough pick up and hurl a Rampardos by the tail.
- Power-Up Food: Played with. During a battle with Palmer, Grotle accidentally swallowed its Energy Ball. The result was a nearly unstoppable Rock Climb that required Rhyperior to slam its tail into the ground to moderately slow Grotle.
- Running Gag: Early on, he shows affection for Ash by biting him on the head.
- Super Speed: Only as a Turtwig. His loss of speed upon evolution was a bit of a Heroic BSoD for him.
- Turtle Power: A turtle based Pokémon.
- The Worf Effect: Torterra never actually won a single battle at all after evolving, unless it was against Team Rocket or a wild Pokémon. Even as a Grotle, he had a fair number of losses under its belt.
Chimchar started off under the ownership of Paul, who captured it after being impressed by the power displayed by Chimchar's Blaze ability against a herd of Zangoose. Paul would attempt to train and battle alongside Chimchar ever since, but was constantly left disappointed being unable to bring out the power of Chimchar's Blaze again, no matter how harshly he trains it. Finally deciding that he's had enough with Chimchar's incompetence, Paul decides to release Chimchar during the Hearthome Tag Team Tournament. However, Ash invites Chimchar to his team just moments after given their previous interactions throughout the former's Sinnoh journey, which Chimchar accepts.
After becoming a member of a new team, Chimchar would go on to becoming Ash's Sinnoh ace winning a vast amount of battles throughout the journey. It would eventually evolve into Monferno after defeating Paul's Ursaring during a battle against his former trainer, and then into Infernape during a battle against Team Rocket. Infernape eventually learns how to control Blaze under Ash's tutelage, and manages to be the one that scores the overall victory for Ash against Paul during the Sinnoh league.
- The Ace: Hands down Ash's strongest Sinnoh Pokémon (and more than likely one of his strongest in general), being a main battler after joining Ash's team early on in the series. It plays a major role in defeating four Gym Leaders, knocking out two of their Pokémon. In Ash's full battle with Paul at Lake Acuity he was the only Pokémon aside from Staraptor to get a win during that battle. After reaching his final evolved form he beats half of Paul's team in the Sinnoh League by himself while taking a crazy amount of abuse and kept getting back up. As an Infernape he only loses once in battle and that loss to was a more experienced Infernape belonging to an Elite Four Member, which is justified given the way Elite Four Members are portrayed in the anime.
- Badass Adorable: As a Chimchar, he was an adorable monkey who was a strong battler.
- Bare-Fisted Monk: Monferno learns Mach Punch upon evolving and it kept the move as an Infernape. When Blaze is activated, the power of Mach Punch also increases.
- Beware the Nice Ones: He's normally very sweet, but if you active Blaze...
- Determinator: Particularly in the Sinnoh League. Infernape, Ash's last Pokémon, is nearly beaten by Paul's Electivire. Paul insults him while Electivire goads him into standing back up. Against all odds, Infernape manages to get back on his feet just as the referee is counting down, and activates Blaze to win the fight.
- The Dog Bites Back: Chimchar was released by Paul after it was deemed too weak by him. Under Ash's ownership, it become his strongest Sinnoh Pokémon and become his trump card during his match against Paul, defeating half of his team.
- Earn Your Happy Ending: Chimchar has a hard time during Paul's ownership and was eventually released after it failed to live up to his expectation. Moments after being released, he joins Ash's group where he made many friends and become stronger to the point he finally earns Paul's respect.
- Everything's Better with Monkeys: Based off of a monkey, and one of the good guys.
- Everything's Better with Spinning: It uses Flame Wheel and Counter Shield by spinning. At one point while using Flame Wheel, it accidentally learns Flare Blitz.
- Expy: His role as an abandoned fire Pokémon taken in by Ash after deemed weak by his former trainer also bears heavily resemblance to his Kanto era Charmander. Thankfully however his evolutions lack as much of the latter's early disobedience (intentionally anyway, see Turns Red).
- Fast Tunnelling: Uses Dig to perform sneak attacks from underground.
- Frickin' Laser Beams: His Flamethrower becomes an utterly gigantic one when he uses Blaze as an Infernape.
- Happy Dance: Would often perform one upon a victory, but would often be immediately curbed by Paul. After overcoming his fear of Zangoose, he's initially afraid to dance again, until he remembers he's with a new trainer, and among new friends.
- Heroic Second Wind: Blaze activates during the final fight with Paul at the Sinnoh League, giving him the strength to turn around the fight and win.
- Hot-Blooded: Despite his experiences, Chimchar still loves to battle, and he only gets more hot-blooded as he evolves.
- How Much More Can He Take?: During his final battle with Paul, Infernape takes a ridiculous amount of punishment but refuses to stay down.
- Nice Guy: Even under Paul he was sweet-natured. When fighting Team Galactic, he took an attack meant for Pikachu from Saturn's Toxicroak, and when Ash felt guilty the next day for letting him get so badly hurt, Chimchar silently expressed that he didn't blame him at all.
- The Power of Friendship: Through Ash's kindness and friendship, Infernape is able to master Blaze when it couldn't even activate it while under Paul's ownership.
- Shoryuken: He usually emerges from Dig doing an uppercut motion.
- Spotlight-Stealing Squad: Got used more and received much more focus than any other Pokémon in Ash's roster.
- Sympathy for the Hero: Since joining Ash, many people take interest in it ranging from Cynthia, Reggie and Zoey. Even Team Rocket has a soft spot for it ever since the Tag Battle.
- Tears of Joy: Seeing how Ash treated it compare to Paul makes the little chimp cry.
- Technicolor Fire: Its Flare Blitz is blue in color in contrast to Flint's Infernape's.
- Training from Hell: Under Paul's ownership, Chimchar receives harsh training from him which involves it being attacked by Paul's other Pokémon in order to activate Blaze which turns out unfruitful.
- Turns Red: When Blaze activates. While in this state, he gains a boost in power, but also enters into a mad frenzy. Coincidentally, his eyes also turn red. Through Ash's support, and maturity as an Infernape, he eventually manages to control Blaze.
- Unstoppable Rage: When Blaze activates, he often loses control.
- "Well Done, Son!" Guy: He constantly tried to seek the approval of his ex-trainer, Paul, and would get upset if he let Ash down (even if the latter was far more understanding).
- Why Did It Have to Be Snakes?: It is greatly afraid of Zangoose as it was attacked by a pack when it was still a wild Pokémon.
- The Worf Effect:
- Its only official loss as an Infernape was against Flint's own Infernape, showing the power level difference between it and an Elite Four's Pokémon.
- In a more Played for Laughs example, he once also suffered a beatdown from Team Rocket's Meowth of all Pokemon to demonstrate The Power of Love after he gained a crush on a Glameow.
- Worthy Opponent: After first evolving, Electabuzz was much less of a Jerkass. His expression during the first 6-on-6 says it all - having seen Chimchar earlier in battle, he's sent out against Monferno. Cue a look of shock, followed by Monferno grinning, which Electabuzz returns. And after Monferno becomes Infernape, the two simply glance at each other and share a smirk. When they fought in their final forms during the Sinnoh League, Electivire no longer sees Infernape as someone he can push around but as a fomidalbe opponent. When Infernape collapses to the ground at one point, Electivire stops the referee from deeming it the winner and tells Infernape to get up, knowing that it is much stronger.
- Wreathed in Flames: When using Flare Blitz, he cloaks himself in fire.
- You Have Outlived Your Usefulness: After failing to activate Blaze and to live up to his expectations, Paul releases Chimchar.
- Voiced by: Kiyotaka Furushima
Buizel lived in a river along the path to Eterna City where he made a name for himself as a powerful opponent for trainers. After hearing about the rumors surrounding Buizel, Ash and company decide to fish in the river for a chance to battle against him, which eventually results in Dawn capturing Buizel. Afterwards, Dawn has some struggles bonding with Buizel due to not being used to having a battle-hungry Pokémon that doesn't have much interest in Contests, but eventually settle their differences.
Further down the line, Zoey notices how in addition to Buizel wanting to take part in Ash's gym-style battles, Ash's Aipom appears to be more interested in Dawn's Contests. She suggests for the two of them to make a trade so that Buizel and Aipom can pursue what they desire, which Ash and Dawn accept. Now under Ash's ownership, Buizel takes part in Ash's gym challenge throughout Sinnoh, becoming one of his most effective battlers.
- Badass Adorable: He's small, he has Cute Little Fangs, and he will kick your tail. His introduction episode establishes him as one by being able to take on and defeat Dawn, Zoey, and Ash's Pokémon by himself.
- Badass Arm-Fold: Buizel typically can seen with his arms folded and completely serious.
- Blood Knight: In his first appearance, Buizel systematically defeated Dawn, Zoey and Ash's Pokémon one after another and still wanted more. He also challenged Lucian after realising that he was part of the elite four. It does hint at where his interests lie.
- Boisterous Bruiser: He's pretty haughty, and it only gets worse the more battles he wins.
- Break the Haughty: Make no mistake, he's a great battler, but he needed to receive a Curb-Stomp Battle from Lucian's Bronzong before he realized he still has quite a ways to improve.
- Character Development: Though Dawn caught him and began using him in contests, it soon became clear that although he enjoyed contests, Buizel wanted to battle even more. In contrast, Ash's Aipom was more of a trickster and wanted to play around more than battle, so Ash and Dawn decided to trade Aipom and Buizel with each other. Afterwards, Buizel shows great prowess in battle.
- Fragile Speedster: Especially when his Swift Swim ability activates. However, Buizel is consistently shown to be physically frail, just like his game counterpart.
- An Ice Person: Knows Ice Punch, and also discovered how to use ice to freeze and enhance his Aqua Jet.
- Irony: He was traded to Ash for Aipom because Buizel is primarily a battler. When Wallace convinces Ash to compete in the Wallace Cup, the Pokémon he recommended that Ash use...is Buizel.
- Jerk with a Heart of Gold: Buizel is this, pre-Character Development. Buizel can be aggressive, aloof and rebellious at times (a bit of a punk). He can also be loyal, dedicated, hard-working and a pretty good guy underneath his bad boy, tough guy exterior. During his short time with his original trainer, Dawn, Buizel quickly became supportive of her dreams and her interests after learning to value her as a trainer (despite Pokemon and trainer having two very different personalities), and acclimated well with the rest of her team (even Piplup) once he lost some of his tude. By "Sandshrew's Locker", he'd mellowed out considerably from his debut in "Buizel Your Way Out Of This".
- Lightning Bruiser: He is capable of taking hits and dishing them out normally, but when in rainy weather, his speed doubles thanks to Swift Swim and he starts dealing out hits with alarming speed and grace.
- Overshadowed by Awesome: In a way. Buizel was originally portrayed as The Big Guy on Ash's team, but after Ash's other Pokémon evolved, Buizel lost this aspect.
- Pintsized Powerhouse: He's tiny, but can still knock around Pokémon many times his size.
- Proud Warrior Race Guy: Very arrogant about his species.
- Spotlight-Stealing Squad: There was a point during the middle of Ash's Sinnoh journey where people felt this way about Ash's Buizel (particularly between gyms 3-5). He was basically Ash's main battler playing a star role against Maylene and Crasher Wake, and also scored a victory against Fantina. He was also the go-to choice when Ash chose to participate in the Wallace Cup during this portion of the journey.
- The Worf Effect: After defeating Fantina's Gengar, Buizel rarely had any standout moments after the portion of the Sinnoh journey where he was viewed as a Spotlight-Stealing Squad.
- Averted when he beat Paul's Gastrodon in the Sinnoh League and managed to put up a better fight against Paul's Drapion than Staraptor and Torterra before going down.
Gligar started off as part of a huge Gligar swarm headed by a Gliscor that were all causing mischief in a town they were trapped in along the path to Veilstone City. Ash and company arrive passing through to reach Veilstone, but decide to help solve the issue by pulling off a plan to blow the swarm out of the town. However, they only managed to pull this off thanks to one of the slower Gligar managing to gather the others all into one place after Paul caught the Gliscor, which left the swarm in disarray and leaderless. The slow Gligar decided to stay behind wanting to continue travelling with Ash, resulting in its capture.
After joining Ash's team, Gligar proves himself to be a silly comic-relief type of the group, but doesn't get to do much early on. After being handed a Razor Fang from Gary, Gligar evolves into Gliscor soon after in order to support Ash in a battle against Team Rocket. As a Gliscor, it keeps the silly persona that it had as a Gligar, but becomes a worthy contributor to Ash's Sinnoh team. Eventually, Ash decides to leave Gliscor in the care of an Air Battle Master named McCann so that it can receive further training as a master of the air, but later gets to return to Ash for the Sinnoh League. After Sinnoh, Gliscor remains at Oak's lab instead of returning to McCann.
- Acrophobic Bird: As a Gligar. It mostly has better luck flying after evolving into Gliscor. Mostly.
- Big Creepy-Crawlies: It is part-bat, part scorpion.
- Bullet Hell: Its Stone Edge attack is portrayed as a large number of stones spiraling around it and then being launched at its opponent in a swarm.
- Bunny-Ears Lawyer: Despite its comedic and sensitive personality, Gliscor is a powerful battler.
- The Bus Came Back: After a 30 episode long absence, it returns in time for Ash's Sinnoh League battle with Paul, and afterwards it is sent to Professor Oak's Lab rather than returning to McCann.
- Butt-Monkey: Mostly in "Doc Brock". In just one episode (in order): it's been ignored; the wind was against it (again); it couldn't Watch Out for That Tree!; and it was left behind (on purpose, because Brock needed to hurry ahead to help Dawn's Pachirisu), only to be completely forgotten until the final seconds!
- Call-Back: Gligar's debut, as part of a delinquent gang of Pokémon that terrorizes a city (think Squirtle).
- Characterization Marches On: Gliscor never uses Screech again, despite learning it in "A Breed Stampede!"
- Character Tics: What sets it apart from other Gligar/Gliscor is its tendency to wink and lick its lips in an exaggerated manner. Both Gligar and Gliscor also like to stick out its tongue for no other reason.
- Dark Is Not Evil: You'd be surprised how sweet Gliscor is despite looking so creepy otherwise.
- Desperately Craves Affection: Gliscor clearly longs for Ash's approval. Fortunately, with Ash being Ash, it ends up receiving it.
- Die or Fly: In Fighting Fear with Fear!, Gligar is given the option of using a Razor Fang to evolve when it desires to become stronger, but Ash prevents Gligar from using it until they do some proper training together. The training is well underway until Team Rocket shows up and their hijinks lead to Ash falling off a cliff, and Gligar can't fly fast enough to stop Ash's descent. Ash, knowing Gligar has earned its prize, tosses the Razor Fang to it and it catches the item, immediately evolving into Gliscor and gaining enough newfound speed to save its trainer from falling to his doom.
- Face of a Thug: Despite its frightening appearance, Gliscor is one of Ash's sweetest and goofiest Pokémon.
- Flight: Unreliable as a Gligar, but gets better and eventually masters it as a Gliscor.
- The Glomp: To the point that it once homed in on Brock when the latter was trying to evade it (and Gliscor still hits Brock).
- The Load: Until it evolved into Gliscor, it was without a doubt the weakest link in Ash's Sinnoh team and never won any battles. Even after evolution it tended to have an unsteady pattern in battle (defeating Byron's Bastiodon, yet falling to Candice's Snover). It finally grew out of this completely - during the battle with Paul, it put up a good battle against Ninjask and managed to defeat his powerful Drapion, which had previously knocked out Buizel, Staraptor and Torterra with ease.
- Not Quite Flight: Though it's a Flying type, most of its flight is gliding rather than powered flight and it has been shown to have trouble taking off on flat ground in still air.
- Plucky Comic Relief: Despite being a competent battler, Gliscor is not meant to be taken seriously. Everything it does outside of battle is meant to be silly.
- Power Up Let Down: Stone Edge can't seem to hit a thing. Averted by Giga Impact.
- Puppy-Dog Eyes: Shows these when upset at losing, rejection or when Ash scolds it, especially when frightened. Often combined with Cry Cute.
- Put on a Bus: Ash leaves Gliscor behind to train with the Air Battle Master in Mastering Current Events!. It eventually returns in time for Ash's rematch with Paul at the Pokémon League.
- Scary Scorpions: Completely Averted! Gliscor is surprisingly adorable.
- Spam Attack: How it defeats Byron's Bastiodon in Dealing with Defensive Types!, continuously spamming Fire Fang like there's no tomorrow.
- Took a Level in Badass: After finishing training with the Air Battle Master. It has mastered Giga Impact, and can glide perfectly, even negating Giga Impact's recharge drawback.
- Watch Out for That Tree!: Since it can only glide (and not even all that well), Gliscor ends up slamming into trees, walls, people, etc.
- What Happened to the Mouse?: Never cleared up whether it returned to McCann, or was deposited on Professor Oak's lab like the rest of the Pokémon before it. It's finally revealed in The Dream Continues! that it was sent to stay at Professor Oak's lab as it was seen during the Group Picture Ending.
- Voiced in Japanese by: Daisuke Sakaguchi
Voiced in English by: Tom Wayland
Gible took the sixth slot on Ash's Sinnoh Team after Gliscor was left with Mccann to help it master Giga Impact. Ash and company came across the oblivious Gible along the way to Daybreak Town where they come across the move tutor, Wilma, teaching Gible how to use Draco Meteor. The gang decides to try to help the Gible learn the move, which results in Gible forming a bond with them, and follows after the gang when they decide to continue on their journey, eventually leading up to Ash capturing him.
Under Ash's ownership, Gible spent the rest of the journey continuing to learn Draco Meteor under his trainer's tutelage, and gets to participate in the Sinnoh League. Gible had also quite a long-lasting running gag where his failed Draco Meteors always somehow come down crashing upon Dawn's Piplup.
- Big Eater: He ate through 2 of Team Rocket's mechas! And Barry's bicycle! And a Shadow Punch from Conway's Dusknoir!
- Character Tics: He has a tendency to bite on people's heads.
- Chekhov's Skill: His habit of biting and not letting go was instrumental in defeating Conway's Shuckle and Dusknoir.
- Dumb Muscle: Gible is noticeably quite dense, but surprisingly powerful. Tobias claims that Gible could have defeated Darkrai with his Draco Meteor if only it made contact.
- 11th-Hour Ranger: Ash only catches him toward the end of the Sinnoh arc.
- Extreme Omnivore: He ate two of Team Rocket's mechas, Barry's bicycle, and a Shadow Punch attack. The only thing he couldn't stomach were Shuckle's sludge bombs.
- Foreshadowing: Ash had previously attempted to catch a separate Gible, who ended up being caught by Khoury. Nonetheless, about 10 episodes later, Ash caught this one.
- Genius Ditz: Looks and acts dull witted much of the time, but was apparently smart enough to use its Draco Meteor to find Piplup a few times.
- Our Dragons Are Different: He's a land shark and is part Ground-type.
- Overly Long Gag: "Gotta get a Gible": his encounter with a Team Rocket mecha involves a drawn-out Beat Panel of an ellipsis five dots long + sweatdrop (approximately a second each dot). TWICE IN A ROW!
- Pintsized Powerhouse: He only comes up to below Ash's knees, but he is capable of taking on opponents 10 times his size.
- Plucky Comic Relief: It ate through Team Rocket's mechs, always scarfed Brock's food, and was very roly-poly.
- Running Gag:
- Draco Meteor has a tendency to hit Piplup and ONLY Piplup prior to mastering it. He exploits this a few times when the trainers are looking for Piplup.
- His tendency to bite onto anything that grabs his interest, and never let go.
- Also invoked; in separate occasions, when a Ditto was impersonating Piplup, and when he was separated from the gang, Gible launches Draco Meteor (without even a command from Ash) just to find him!
- The Stoic: But he's not emotionally reserved. He's just...vacant.
- Took a Level in Badass: Upon mastering Draco Meteor, he became one of Ash's most powerful Pokémon. Even Tobias pointed out that his Olympus Mons Darkrai would've been defeated by it if its attack connected.
- Tunnel King: Above ground, he's a little quicker on his feet than he looks. But underground is where he's truly in his element.