%% Image Pickin' thread: http://tvtropes.org/pmwiki/posts.php?discussion=1486147231088787700
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[[quoteright:347:[[Webcomic/BobAndGeorge http://static.tvtropes.org/pmwiki/pub/images/Won.jpg]]]]
[[caption-width-right:347: I guess I could retire? ...Oh right, the plan.]]

->''"Could this be... our first taste of victory?"''
-->-- '''Jessie''' (as Team Rocket finally defeats [[TheHero Ash]] in a fair battle after [[LongRunner 951]] episodes), ''Anime/{{Pokemon}}''

Some antagonists are expected to be only a minor threat to the story's main characters, something they can be expected to defeat time and again. Threats that the heroes have dealt with many times before, and are used to show how much they have grown, because those antagonists are annoyances at best.

Except something happened, and they're ''not'' minor threats anymore.

These minor antagonists have found some way to penetrate the main character's defenses, through some sort of {{Upgrade|Artifact}} or {{Training|FromHell}}. Or they're used to introduce new characters, by beating them so badly that the heroes [[PursuedProtagonist must come to their aid.]]

Regardless of how these antagonists win, it serves as a call to training/focus by the protagonists, after which, the antagonists are defeated as easily as they were before the Team Rocket Win.

Note that the antagonists ''must win then lose again'' in order to qualify. If it looks like they will win but are defeated at the last minute, then that's a NearVillainVictory. If the bad guys win and the work ends, then it's also TheBadGuyWins. If the hero sees the bad guys win in the future, then it's a BadFuture. Contrast BigBadWannabe, which may at times overlap.



[[folder:Trope Namers]]
* Team Rocket, the {{Trope Namer|s}} from ''Anime/{{Pokemon}}'', beat the crap out of Ash's Pokémon when they were allowed to run Viridian City's Gym using Giovanni's Pokémon, at least until Ash managed to regain momentum and beat them at their own game. There have been a few other instances where Team Rocket has been successful in battle, but it was because they were [[RedemptionPromotion trying to do something good for a change]]. Their victories never lasted too long, and they were often sent flying at the end of the episode anyway.
** Jessie (while under her Jessilina alias) has actually become competent enough to win Pokémon Contests all on her own without cheating (though she has considered it at times.) She lost out on winning her fifth ribbon needed to get into the Grand Festival, but Dawn (or rather, a Dawn lookalike by the name of Princess Salvia, [[ItMakesSenseInContext long story]]) gave her the sixth ribbon she had just won. Jessie gratefully accepted it and made her way to the semi-finals against Dawn in the Grand Festival.
*** She had a similar run in the Kalos Showcases (under her Jessilee alias), winning three Princess Keys to get her into the Master Class tournament (which were implied to have all been won legitimately). Much like the Sinnoh Contests, Jessie lost to Serena, but was a popular opponent who made it to the Top 4 in the semi-finals.
** In ''Off the Unbeaten Path'', James won a contest that involved teamwork with one's own Pokémon. He used Mime Jr. and was steadfast in playing by the rules despite Jessie's repeated attempts to encourage him to cheat. So this goes with the "Team Rocket can win if they act like good guys" rule.
*** ''Nearly'' happened when James turned out to be an expert at a sport that used flying Pokémon. Once again, he refused to cheat, and he lost by only the tiniest margin.
** Meowth, who is usually a pitiful battler, once defeated a rival Persian in a one swipe knockout. He also managed to defeat Brock's Onix in a tournament for ownership of Togepi ([[CombatPragmatist albeit by throwing water on it first]]). He ''decimated'' a fair share of Team Plasma's Pokemon single handedly in an EnemyMine as well, while ThePowerOfLove once allowed him to take down several of both his foes and allies' Pokemon ''all at once'' with some Fury Swipes of Love.
*** Meowth also tends to participate with Jessie in contests and showcases, sometimes helping her with the entries she wins. His culinary skills in particular often help garner her popularity.
** Interestingly, repeated encounters with Ash and friends has been like TrainingFromHell to the team, giving them [[MadeOfIron superhuman damage resistance]], among other things. Meowth himself commented that a powerful electric cage was nothing compared to Pikachu's electric attacks. They also learn from their mistakes, though in the process, usually make new ones. An example would be Charmander's debut episode all the way back at the very start of the original series; they use rubber coated equipment to nullify Pikachu's electric attacks, but didn't bring any ''fireproof'' equipment.
*** Heck, in some later episodes, Team Rocket actually does some heavy damage to other trainers. In general, Team Rocket manages to win when the plot requires it - Jessie fighting her way to the end of the Princess Festival tournament, Jessie and James defeating the Eevee Brothers, etc. In fact, during the Princess Festival example, Jessie used her newly-caught Lickitung to achieve a NearVillainVictory against Misty in the final round.
*** A recurring plot twist is Team Rocket actually having Ash and his friends on the ropes until the Pokemon of the Week [[DeusExMachina appears or evolves and pretty much does all the work for them]]. If Ash had to fight them standalone, he'd likely have lost in multiple instances.
** This occurs even in early episodes-- in "The Punchy Pokémon", various trainers are participating in a Fighting-type only tournament. Though Ash beats them in the end, the trio very successfully steals a Hitmonlee and thrashes their competition with it through a combination of regular battling and standard cheating. This is pretty notable, since they beat a Hitmonchan raised by a trainer who LEFT HIS FAMILY to train it.
** In ''The Thief That Keeps on Thieving!'' they actually managed to [[http://www.youtube.com/watch?v=aQjyJY7iEVg catch the wild Pokémon]] that the character of the day was after and send it to their boss. Of course, he sends it back to them and it promptly evolves, giving Jessie a new Yanmega. Said Yanmega then proceeds to get as close as any Team Rocket Pokémon has to blasting off Ash & co.
** They seem fairly competent whenever they are not dealing with Ash and co. - remember that they had wanted posters with their first appearance? - and many of their plans worked… until Ash got involved. According to Pokémon Chronicles, Jessie and James weren't just competent, they were THE BEST operatives in Team Rocket history! In fact, in their first appearance they managed to not only steal ALL the Pokémon in the center (owned by full fledged trainers) and wreck the place, BUT would have gotten away scot-free if not for Ash using a team of Pikachu to supercharge his own! Then... they stopped doing real evil in favor of following Ash around and trying to steal his Pikachu.
** In the ''Best Wishes!'' series, they got new uniforms because of a PROMOTION.
*** Even wilder, they became competent and so far have ''stayed'' that way. They almost capture Pikachu and Iris's Axew. Key and operative word: almost. During a good bunch of that season, they didn`t blast off as usual (the blasting off role was taken by a Sandile who appeared in a couple of episodes). They generally stay away from Ash and company, however, because of their new mission.
*** During that season, Giovanni gave them one mission. The goal of said mission was to collect dream energy from an abandoned research facility in order to help with Team Rocket's plans to conquer the world. While they failed to capture the Pokémon of the day, the episode where they put this plan into action basically ended with Giovanni congratulating them on succeeding and telling them that he had people looking at the energy to see what they can do with it. That's right, Team Rocket just successfully completed the first step in a plan for world domination.
*** In a two-parter based in the Nimbasa City subway system, they pull out ''all'' the stops - not kicking off their plan until Ash and his friends arrive, with Meowth having [[HeelFaceMole faked joining them]] in order to lure them into a Pokemon center where he could steal Pikachu and all the other Pokemon and load them on the subway train. The heroes catch up to their train...which is revealed as a decoy. The Subway Bosses try to track the train...only for multiple signals to show up on the monitor, throwing them into confusion. When Pikachu and the other Pokemon try to break free on their own, Team Rocket's scientist commander flies a helicopter on over to the train to ''air-lift'' it and the Pokemon up so that they can't escape. The heroes just ''barely'' come out on top, and even Cilan admits that this was one of Team Rocket's finest plans.
*** A great example of this occurs in the Kami trio two parters. In the first, they set in motion the appearance of two of the legendary Pokemon, and then wait for Ash, since they know that he'll show up. Then they use him and his friends to summon Landorus. ''They are GenreSavvy enough to use the fact that Ash attracts legendary Pokemon to their own advantage.'' In the second, they locate an undersea ruin and are able to help Giovanni capture Ash, the gang, and Meloetta, who is the key to summoning the Kami trio again. They came close to taking over the Unova region, but Giovanni got possessed by the reflecting mirror used to transform the Kamis into their Therian Formes, and Team Rocket had to actually help the twerps break the possession before Giovanni destroyed, rather than took over, the world.
*** In the N Saga, though, they fell back into their old comic routine because of negative fan reaction to their new serious attitude. And by ''X & Y'', they had pretty much lost all their competence, going back to being the butt monkeys.
** "Dressed For Jess Success" and "A Dancing Debut" stand as the only episodes with them officially the "winner" over a member of Ash's team however (in both cases, the female companion in a performance contest). While the heroine in both instances is a GracefulLoser, nothing about the trio's victory is tainted or negated and they end the episode feeling rather pleased with themselves, par a bit of light hearted squabbling over their glory.
** "Holy Matrimony" gets special mentioning, since Jessie and James actually make it out of the episode's dilemma rather gracefully (albeit with Meowth left chasing) while Ash's team are left behind to suffer the EndOfEpisodeSilliness instead.
** In the musical ''Theatre/PokemonLive'', Jessie and James actually brought Pikachu to Giovanni, and they suffer no consequences for it.
** The most literal example of this trope happens in episode 12 of the 20th season, when Team Rocket ''finally'' manages to defeat Ash in battle. Jessie's Mimikyu even tries to attack Ash's Pikachu while it's down, and the only thing stopping Team Rocket from making off with it is the wild Bewear that was following them around.
** Episode 25 of the above series had Team Rocket successfully obtain a Darkinium Z-crystal by defeating a Totem Raticate.

* A Geico spot with the characters from ''WesternAnimation/HeManAndTheMastersOfTheUniverse'' has Skeletor distracting He-Man, She-Ra and Man-At-Arms with the sales pitch "Switching to Geico could save you hundreds on car insurance" long enough for him to make a clean getaway.
-->'''Skeletor:''' Catch you on the flip, suckers!

[[folder:Anime & Manga]]
* In ''Manga/SchoolRumble'', Tennouji beats Harima once when the latter was in despair after finding out Tenma liked Karasuma…[[VictoryIsBoring though he wasn't able to enjoy it because of how easy it was.]]
* A borderline example. In ''Otasukeman'', one of the series from the ''Anime/TimeBokan'' meta-series, at the end of every episode the chief of the Time Patrol asked the two main groups of the Patrol to pick a choice between two special kinds of training. One group (who really were the heroes of the series, the titular Otasukeman, and always won the battles) always picked the pleasant, relaxing activity, when the other one (who really were the TerribleTrio, the "evil" Ojamaman, and always lost against the Otasukeman) always picked the nasty, gruesome TrainingFromHell. In one episode, however, the Terrible Trio chose wisely and won a nice boat trip over a calm river, while the heroes found themselves in a Japanese cemetery filled with angry ghosts.
** In Ippatsuman, another sub-series from ''Time Bokan'', the incompetent TerribleTrio with no superpowers manage to seemingly beat the titular FlyingBrick Superhero. However this ends up {{Subverted}}, not only was it actually the threatening SuperVillain that was the one who actually killed Ippatsuman with the Trios attacks having no effect, but [[spoiler: it was [[ActuallyADoomBot a Robot Decoy of the SuperHero that was destroyed.]]]]
* ''Anime/SonicX'' had this happen once, but not when facing Sonic. Usually Eggman's schemes fail miserably, and his machines and robots are useless, but then he goes up against some Metarex that are attempting to hurt Sonic. Without warning, Boko and Deko, his worst robots, become super strong and beat everyone down, and Bokkun delivers a powerful uppercut kick, clearing a pathway for them all. On several occasions, while never outright defeating Sonic, Eggman managed to distract or overpower him long enough to get away with a Chaos Emerald. He actually gets his hands on all seven at least twice over (though on both occasions uses them on a [[AIIsACrapshoot haphazardous death machine]]).
* At the end of the first arc of ''Anime/DigimonXrosWars'', [[spoiler:Bagramon easily takes all the Code Crowns and reconfigures the Digital World. Taiki, Akari, Zenjirou, and Shoutmon are blown back to Earth. While they're gone, Kiriha and Nene are forced into hiding, Xros Heart is captured, and the Digital World comes under worse oppression than before.]]
* ''Manga/TentaiSenshiSunred''
** Florsheim once brought a werewolf to do battle against Astro Fighter Sunred… On an overcast night. After spending several hours waiting for the beast to transform, [[ScrewThisImOuttaHere Sunred had had enough and went home]]. Vamp wonders if they can call this a 'win' until one of his combat goons tells him they probably can't.
** In another story, new, more evil-oriented villains invade the neighborhood, only to discover that the Florsheim minions are {{Not So Harmless Villain}}s. Armor Tiger [[IAmNotLeftHanded wasn't even wearing his armor at the time!]]
* Happens at least once per season in the ''Anime/PrettyCure'' franchise, whenever TheDragon of the BigBad faces the heroines before TheDragon gets hit by TheWorfEffect or VillainDecay.
* Happens during [[WhamEpisode episode 26]] of the first season of ''Anime/FushigiboshiNoFutagoHime''. [[spoiler:Prince Shade reveals a tremendous amount of badassery but is too late to stop the [[EvilChancellor Minister's]] goons from stealing [[TheForce the Prominence]] from Fine and Rein. [[SadisticChoice What's worse is that he had to save]] [[DistressedDude Prince Bright]] [[SadisticChoice from falling to his death and therefore let the goons get away with the Prominence.]]]]
* In ChihiroKagachiAndTheBogeymen, [[RunningGag Doctor Zweiback actually got a one-dollar bill from Hinata]] because Hinata had slipped on a banana peel.
* In the ''Anime/SDGundamForce'' episode "Attack of the Big-Zam!", the Dark Axis Trio use the titular super-tank to attack the SDG Base, planning it to bring it down onto Neotopia. And though the SDG is able to move the base away from the city, the base ''still'' comes down...right onto the Big Zam itself, trapping the Trio and putting them out of commission for the rest of the arc. However, they still accomplished their mission, and with the SDG away to do repairs, the rest of the Dark Axis is able to invade Neotopia ''en masse''.
* [[SympatheticInspectorAntagonist Zenigata]] does actually catch ''Franchise/LupinIII'' from time to time, which usually leaves him realising that VictoryIsBoring. Of course, getting Lupin to ''stay'' in prison usually turns out to be just as hard as catching him.

[[folder:Comic Books]]
* Anytime The Shocker does anything right, it counts as this. But what stands out in particular was his appearance in the ComicBook/UltimateSpiderMan book, where after countless, effortless losses to Spidey (who slammed the point home by cracking jokes), he managed to knock him unconscious. He then tied him up with chains, ranting and torturing him, and likely would have killed him if not for Kitty Pryde and the NYPD finding his location.
* SpiderMan has been beaten by [[IneffectualSympatheticVillain Stilt-Man]] ''twice''. (Spidey himself rates the two incidents as numbers 3 and 4 among his "10 Most Embarrassing Moments" in ''Spectacular Spider-Man Annual #12''.)
* In ''WesternAnimation/ThePowerpuffGirls'' story "Smart And Smarter" (Cartoon Network Block Party #59), Mojo Jojo outwits Blossom, with her sisters' blessings! Blossom ([[InsufferableGenius who let her ego swell after being admitted to a special school]]) blows her ice breath which Mojo counters with a heat shield. The trail of melted ice reaches Blossom's foot (which she doesn't see) and she emits static electricity from her hands which in turn fries her to a frazzle. The ending panel has Buttercup shaking hands with Mojo.

[[folder:Fan Works]]
* ''FanFic/MagicalTroubleshootingCrossoverFightingFederationUltra'', a tournament with a crossover cast of various anime series, actually has Team Rocket win at least once, much to their own shock.
* The second season's arc of ''FanFic/LaSerieDeKen'' is kicked precisely because of this, Team Rocket manages to steal all but one of Ken's Pokémon and he has to start anew with a new set to try to recover them, it also marks the start of the villains as NotSoHarmlessVillain and the series' CerebusSyndrome.
* A ''Powerpuff Girls'' picture strip story, "Diet With Honor," had Mojo Jojo making good on a threat to give Blossom "the spanking you so richly deserve."
* Done with some of the early villains in both ''[[FanFic/UltimateSleepwalker Ultimate Sleepwalker: The New Dreams]]'' and ''[[FanFic/UltimateSpiderWoman Ultimate Spider-Woman: Change With The Light]]'' as a means of averting VillainDecay. Some of the earliest villains Sleepwalker and Spider-Woman have fought later defeat the heroes, or defeat other villains, to maintain the badass credentials of the entire RoguesGallery and make the very clear point that the SortingAlgorithmOfEvil does ''not'' apply in these two series.
* In ''FanFic/MegaManDefenderOfTheHumanRace'', in episode 9 Cut Man, Guts Man, and other Robot Masters defeat Mega Man.
* In the Website/DeviantArt entry here, a Xena-like heroine surrenders to a kobold simply out of pity. (''NSFW''' so [[http://maplewarriorofxeen.deviantart.com/art/Conquered-PG1-637392667 view it here with caution]].)
* The Pokemon story ''FanFic/CommonSense'' is all about giving Team Rocket a level in badass and becoming a more serious threat from its very first appearance in the canon series. While Jessie, James and Meowth don't win every single time they encounter Ash, they are so devastating in their wins that they have become Ash's personal KnightOfCerebus brigade.

[[folder:Films -- Animation]]
* In ''WesternAnimation/{{Cars}}'', when Lightning brakes hard at the finish line, reverses, and pushes "The King" across. This time, however, when Hicks wins, he's the only one celebrating and is shocked when everyone starts booing him. Since he cheated by (intentionally?) wrecking "The King" in the first place, he had no business being shocked.
* ''WesternAnimation/{{Megamind}}'''s plot starts rolling because of this, which is lampshaded by both Megamind's sidekick early on and [[spoiler:Metro Man]] much later.
* Zig-zagged with ''Disney/WreckItRalph''. The title character, a figure in a 30-year-old video game is tired of being the "bad guy" and schemes to get a medal to prove he can be a good guy. After accidentally landing in another game, "Sugar Rush," he helps an outcast little girl, Vanellope Von Schweetz, win a race, but he has to deal with the game's evil boss and a swarm of cy-bugs which were brought in from another game to this one.

[[folder:Films -- Live-Action]]
* In ''Film/TheGreatRace'', the main character Leslie stops just short of the finish line and lets the HarmlessVillain team win to show TheChick that he loves her enough to give up the race. Professor Fate becomes ''livid'' about this, and challenges Leslie to another race, despite having spent the ''entire run of the film cheating as hard as he could physically manage,'' because he wanted to win on his own terms and not have it handed to him.

[[folder:Live-Action TV]]
* Presuming that the condition for villain victory is "kill the slayer", ''Series/BuffyTheVampireSlayer'' has numerous examples: Spike legitimately out-fights and kills two Slayers, Drusilla effortlessly takes out Kendra the Vampire Slayer, The Master kills Buffy on two occasions (one time she is revived and the other in an alternate universe), and a random vampire nearly kills Buffy in "Fool for Love", and it's Riley that ultimately puts him down.
** Even ''Harmony'' (probably the biggest joke on the show) managed to kill a Slayer in the episode "Harmonic Divergence" (although it was at least partially by accident) and she had a more earned victory in "Harm's Way" against another vampire (that one was technically a case of EvilVersusEvil, but she was clearly the lesser evil.)
** If you count characters who ''nearly'' pull off kills until [[DeusExMachina somebody saves them at the last second]], then that opens up a much larger group, including [[spoiler: the Gentlemen, Warren, Dark Willow, and Caleb.]]
** Glory kicked Buffy's ass all over season five. Willow was the only one who managed to do any true damage to her. Well, her and Giles, but that was only because he [[spoiler: killed her human host while she was essentially unconscious]].
* ''Franchise/PowerRangers''
** In ''Series/MightyMorphinPowerRangers'', Zedd and Rita would pull this off at least once a season. This usually involved the zords being destroyed and re-formed, and as such, usually happened when they had run out of Sentai footage and/or just in time for an action-figure shopping season. Topped by the series finale of ''Mighty Morphin'', as the two actually do succeed in not only leaving the Rangers powerless, but also ''destroying'' the Command Center. Damn.
** In ''Series/PowerRangersTurbo'', Divatox does the same thing.
** ''Series/PowerRangersInSpace'' has an all out attack on the galaxy with the Space Rangers and their allies all losing. They only survive because of [[spoiler: Zordon's HeroicSacrifice]].
** And in ''Series/PowerRangersLostGalaxy'', Psycho Pink manages to actually kill a Power Ranger. She stabs a morpher with the Savage Sword, which created a massive vortex that threatened to destroy Terra Venture. The only way to stop it was [[spoiler: Kendrix]] crawling inside and hitting it with the Quasar Sabre which killed [[spoiler: her]]. Of course Psycho Pink is quickly defeated by the other rangers in their Megazord.
* ''Series/DoctorWho'' had the episode "Victory of the Daleks", which was exactly what it said on the tin; that is to say that the Daleks managed to accomplish their main goal and escape to tell the tale.
** Technically, "Asylum of the Daleks" pretty much counts as a win: the Daleks got the Asylum destroyed and all got to live at the end, retaining their (implied) massive space empire, too. They ''do'' lose all their memories of the Doctor, but then [[StatusQuoIsGod get those back]] [[Recap/DoctorWho2013CSTheTimeOfTheDoctor in short order.]]
* ''Series/StarTrekTheNextGeneration'' had the episode "Data's Day", where the Romulans managed to win one of the series' tense Neutral Zone stand-offs, recovering their spy and forcing the ''Enterprise'' to retreat. This is lampshaded by Commander Riker who notes "Some days, you get the bear; some days the bear gets you."
* The ''Series/StarTrekDeepSpaceNine'' episode "Our Man Bashir" combined TeleporterAccident and HolodeckMalfunction to recast several of Bashir's crewmates as characters in his Franchise/JamesBond-esque spy holonovel. The holonovel's script is intended to play out with either the HotScientist or FemmeFataleSpy being killed, and Bashir killing the BigBad in retaliation, but as doing so could kill his crewmates, Bashir decides that the only way to win (i.e. rescue them) is to allow the BigBad to win.
* The ''Series/{{Charmed}}'' ones don't always get away without a scratch. The list is actually quite long:
** Inspector Rodriguez comes very close in the season 1 finale which has a time loop. Phoebe is killed in the first loop and Piper as well in the second. The only thing that helps the sisters is that Phoebe gets strong deja vu vibes whenever time resets.
** Ginny in "I Dream of Phoebe" wishes the sisters dead. Of course they're still around as ghosts to ensure they don't stay that way. One of them possesses Ginny and tricks her into wishing them alive again (''Aladdin'' rules don't apply here).
** When Prue is turned into a teenager without her powers, she falls victim to a Dragon Demon and again has to be wished alive by a genie.
** Phoebe and Paige are killed during a fight with Billie and Christy when the powers being used causes the manor to explode. Time Travel and Billie's projection power come in handy to ensure that it doesn't stay that way.
** Phoebe and Paige are killed again in "A Witch In Time" when a warlock is able to strip them of their powers and incinerates them. Piper only narrowly escapes when Leo intervenes.
** Quite possibly the most successful of all. The upper level demon Shax managed to kill [[spoiler: Prue]] at the end of season 3. [[KilledOffForReal For good]]. In the same episode, [[spoiler: Piper]] was also shot dead by a simple human.

* Lampshaded in Billy Preston's "Will It Go 'Round In Circles":
-->I got a story, ain't got no moral,\\
Let the bad guy win every once in awhile.

[[folder:Pro Wrestling]]
* In Puerto Rican pro wrestling, it was a tradition to put men such as Stephano and Tom Danniels in a women's division for a time [[TheWorfEffect solely to show off how strong the women were]] (Danniels was a ''World Champion!''). However, exoticos Barbie Boy and Queen Adonis actually won women's gold in the International Wrestling Association and New Revolutions Wrestling Lucha Libre.
* After Seth Rollins betrayed SHIELD-mates Roman Reigns and Dean Ambrose to join Evolution, and then went on to win the Money In The Bank briefcase, he declared would face a special opponent, worthy of his greatness, in an exhibition match. In true dickhead heel fashion, the "mighty" opponent he picked was notorious jobber, Heath Slater. But Dean Ambrose was still ''incredibly'' bent out of shape over Rollins stabbing him in the back, and shortly after the match started, came down to the ring to heckle Rollins and mess with the Money In The Bank briefcase. These distractions kept letting Slater get the upper hand temporarily, and ultimately lead to Staler pinning Rollins in the middle of the ring, to the ''extreme'' delight of the crowd, and Ambrose absconding with the briefcase in order to further screw with Rollins.
* While he was working for Wrestling/FightingOperaHUSTLE, Wrestling/YoshihiroTajiri decided to invade Wrestling/NewJapanProWrestling, by himself, and managed to force his way into the 2009 G1 Climax. Despite failing to advance after finishing last in his block, he did manage to defeat the reigning IWGP Heavyweight Champion Wrestling/HiroshiTanahashi!
* When Wrestling/{{WSU}} was acquired by Beyond Wrestling, they proceeded to run over the Beyond Roster, including sweeping the guys in a face off. When Wrestling/{{CZW}} acquired WSU, the Juicy Product actually won the {{tag team}} title belts though.[[/folder]]

[[folder:Video Games]]
* ''Franchise/{{Disgaea}}''
** Losing to the MiniBoss in ''VideoGame/{{Disgaea|HourOfDarkness}}'' gives you a [[NonStandardGameOver "secret ending"]].
** Losing to Axel in ''VideoGame/{{Disgaea 2|CursedMemories}}'' at any point nets you [[NonStandardGameOver an ending as well]].
** Losing to Raspberyl in ''VideoGame/{{Disgaea 3|AbsenceOfJustice}}'' also gives you [[RuleOfThree an ending]].
** Happens yet again with Axel in ''VideoGame/{{Disgaea 4|APromiseUnforgotten}}''. [[spoiler: And when he wins this time, he ''[[TakeOverTheWorld really]]'' wins.]]
* In ''VideoGame/FinalFantasyVI'', Kefka's triumph [[spoiler:in Thamasa]] is a complete surprise to the player. After all, almost every other encounter has consisted of Kefka casting a weak spell and then running away, and when Kefka seems to finally be serious in Narshe, he is still quite beatable. So when he appears in [[spoiler:Thamasa, destroying Espers left and right]], there is really no precedent. And right after that, [[spoiler:[[ApocalypseHow Kefka destroys the world]].]]
* ''VideoGame/{{Touhou}}'' has this in the handful of games that you can actually play as Cirno. Or, you know, if you lose to Cirno in the regular games. Cirno's plotlines generally have nothing to do with anything actually going on, and involve her just trying to prove she's "the strongest".
** Meiling is usually the ButtMonkey of the Scarlet Devil CastHerd, but playing as her in ''Unthinkable Natural Law'' and actually winning makes her declare to her friends that [[CrouchingMoronHiddenBadass she was holding herself back and playing the fool all along, waiting for a truly dire situation to reveal herself]]... [[UnreliableNarrator not that you can necessarily trust that statement]].
** In ''Great Fairy Wars'', Cirno is the main character. While she mostly spends the game fighting her fellow fairies (hence the name), the EX stage boss is [[PersonOfMassDestruction Marisa]]. Since canonically the main character(s) always win...
* In ''VideoGame/StreetFighterII'', once you can play as M. Bison, this trope can apply. If you win as Bison, his armies take over the world.
* In the Dreamcast and [=PS2=] ''WesternAnimation/WackyRaces'' game, the final unlock is the ability to play as Dick Dastardly. It's worth going through all the trouble to do so just to win a race as him and hear the announcer's bewildered or disgusted reaction.
* Team Skull from ''VideoGame/PokemonMysteryDungeonExplorers of Time/Darkness/Sky'' was introduced as an [[WarmUpBoss easy first boss]]. In a later mission where your team is sent out to get Perfect Apples however, Team Skull brings their leader along to defeat your team, and then they take the apples you were supposed to find.
* In ''VideoGame/{{Paper Mario|64}}'', Bowser once again starts the game's story by invading Princess Peach's castle. Peach sends Mario on him, [[TheGoodGuysAlwaysWin predicting the usual result]]. Then Bowser pulls out the newly stolen Star Rod, boosting his strength. Cue a HopelessBossFight where your only choice is to let Bowser chalk up his first canonical victory against the plumber. Peach and even Bowser himself are completely astonished.
* ''Franchise/SonicTheHedgehog''
** In a similar manner, Dr. Eggman starts off the events of ''VideoGame/SonicUnleashed'' by depowering Sonic ''in his super form'' and using his power to activate a laser to create an EarthShatteringKaboom. Keep in mind no other villain ([[VideoGame/Sonic3AndKnuckles bar Knuckles technically]]) has actually defeated Super Sonic.
** Playing E-102 Gamma's story in ''VideoGame/SonicAdventure'' allows you to battle and win against Sonic in a brief mini boss. Amy stops him just short of finishing the job however.
* In the ''Franchise/CrashBandicoot'' PartyGame ''Videogame/CrashBash'' it is possible to win Adventure Mode as Dr. Cortex or one of his cronies, giving a bad ending where Uka Uka gains ownership of all of the crystals [[EvilIsHammy "and all of the POWER!!!"]]. This is done in a more direct sense if you play the Adventure Mode in two player co operative with a good and evil player, allowing access to a hidden deathmatch where the two of you fight to determine the ending, thus get the extra reward of kicking Crash or Coco's ass as one of the RoguesGallery before taking over the world.
* Since they're playable characters, it's possible in the ''Manga/RanmaOneHalf'' video games for even complete scrubs like the Card King to kick everyone's ass and, at least in theory, get what they've been after all this time. Since the source material is a SadistShow, of course, [[StatusQuoIsGod it never really works out]] -- with the exception of [[DefeatMeansPlayable Herb]], who [[spoiler: successfully conquers the world]].
* ''VideoGame/KingdomHeartsII'' introduces Pete, who spends the first half of the game as a HarmlessVillain who Sora and his friends encounter several times and easily defeat, and he even gets ADayInTheLimelight in Timeless River. However, during the events of [[Franchise/PiratesOfTheCaribbean Port Royal]], Pete finally scores a victory against Sora through an alliance with Captain Barbossa, [[NotHisSled capturing Will and denying his demands]], and leaves the Keybearer tied up and left to die on a ship rigged with gunpowder.

[[folder:Web Comics]]
* The page picture comes from ''Plague's Misadventures'', one of the hosted comics in ''Webcomic/BobAndGeorge.'' Sigma, who in this series is pretty much a nuisance HarmlessVillain, actually succeeds in bringing down the space colony and bringing about the end of the world when the heroes shoot it down with the giant canon.
* The Dimension of Pain demons from ''Webcomic/SluggyFreelance'', from their [[http://www.sluggy.com/comics/archives/daily/980428 inception]], had been largely {{Harmless Villain}}s. When Torg wound up in their dimension, he easily withstood their attempts at torture, outwitted them, and escaped. After that they repeatedly tried to recapture him every year, but they could only send one demon at a time, only on Halloween night, and it could only stay until sunrise, and they inevitably failed in humiliating ways, to the point where Torg threw Halloween parties with the demons advertised as the main attraction. Throw in their wacky antics during the "[[BSideComics Meanwhile In The Dimension of Pain ...]]" strips, and no one really took them seriously. Then "[[CerebusSyndrome That Which Redeems]]" came along, and with the demons finding a way to bypass their previous limitations, suddenly they're conquering entire countries, butchering helpless bystanders, and outnumbering Torg 1000 to 1. Not to mention [[spoiler:[[KilledOffForReal killing off]] Alt-Zoe]].

[[folder:Western Animation]]
* In the Joe Oriolo WesternAnimation/FelixTheCat TV cartoons, the villains, Professor and Rock Bottom, [[TheGoodGuysAlwaysWin are always trumped by Felix]], be it through his intervention, their sheer incompentence or just pure bad luck. But wheras Professor, Felix's main nemesis, [[FailureIsTheOnlyOption never once scored a victory over Felix]], Rock Bottom actually did manage to score a victory over Felix in "Penelope the Elephant"--[[MeaninglessVillainVictory but even that victory doesn't pay off for him in the long run]]. The episodes plot is centered on the eponymous elephant who has gotten lost from her Rajah, who offers a 50,000,000 bakshee reward for her return. Felix finds Penelope and intends her safe return, but Rock Bottom gets word about the reward, kidnaps her and ties up Felix, and makes it to the Rajah's palace to claim the money reward before Felix can stop him. He is promptly given it by the Rajah--but it turns out that thanks to foreign exchange rates, 50,000,000 bakshees [[RidiculousExchangeRates is only worth 10 cents in American money]]. Rock Bottom is so flabbergasted at this outcome, that he angrily throws the meager award aside and goes into shock, while Felix gets the last laugh.
* ''WesternAnimation/BatmanTheAnimatedSeries''. [[Recap/TheNewBatmanAdventuresE21MadLove "Mad Love"]] has Harley Quinn manage to use one of the Joker's plots to capture Batman and have him dead to rights. This being [[MadLove Harley Quinn,]] Batman manages to play on her insecurities and call Joker. [[TheOnlyOneAllowedToDefeatYou That goes down as well as you'd expect.]]
* ''WesternAnimation/ThePowerpuffGirls'' has instances where the villans win:
** The episode "Meet the Beat Alls" had Mojo Jojo, Princess, Fuzzy and Him team up into an ultra successful band, the "Beat Alls", which the Girls were powerless to beat conventionally. Enter [[YokoOhNo Moko Jono]]. True, Him is hardly a HarmlessVillain, but Fuzzy, Princess and Mojo ([[DependingOnTheWriter at times]]) are pretty low on the threat scale.
** In "Mr. Mojo's Rising", Mojo acquired the Girls' abilities and defeated them, only to launch into a [[ContemplateOurNavels navel-gazing session]] so severe that he didn't notice the Girls recover and turn him back to normal.
** The episode "You Snooze You Lose" even had '''''[[GoldfishPoopGang The Amoeba Boys]]''''' on the verge of victory, albeit ''completely by accident'', obliviously setting the Girls into a trap they stole from Mojo Jojo (until Mojo himself stopped the trap).
** In "Him Diddle Riddle", Him challenged the girls to solve a series of riddles on time to find Professor Utonium or the professor would have to "pay". They found the Professor a few seconds too late and Professor Utonium had to pay... [[spoiler: the diner bill. It was just a diner bill but, the villain won and the narrator didn't have anything to say when he'd usually say the day had been saved.]] It turns out to be a tainted victory however [[spoiler: when Professor Utonium vows to never come to his diner again because the food was terrible, leaving Him to beg him not to leave, promising to make his pancakes taste better.]]
** The episode "Moral Decay" has one concerning almost ''every single villain'' in the series. After Buttercup gets greedy when she realizes she can get money from the Tooth Fairy, she starts collecting villains' teeth from fights. She soon resorts to randomly beating them unprovoked. The other girls find out and organize a surprise attack on her, where the RoguesGallery literally kick her teeth in.
** The SeriesFauxnale, "See Me, Feel Me, Gnomey" began with the city besieged by the girls' RoguesGallery, and the girls getting their butts kicked to set up the main plot.
* ''WesternAnimation/EdEddNEddy''
** While The Kanker Sisters ''always'' seize the day away from the Eds, there are a few expections. For example; "A Fistful of Ed" where Eddy successfully ''scares'' the Kankers away before they begin their usual "affection".
** "A Glass of Warm Ed" and "Dim Lit Ed" however end with the Eds successfully [[EarlyInstallmentWeirdness making a profit out of one of their scams]]. The "Big Picture Show" finale also ends, in a [[CrowningMomentOfHeartwarming rather heartwarming way with the Eds finally becoming popular after the kids saw the Eddy's brother made Eddy the way he was.]]
** "Sir Ed-A-Lot" also ends with them turning the tables on BrattyHalfPint Sarah, [[HoistByTheirOwnPetard capturing her in her own home made dungeon]] after she forces them to go along with princess role play.
* ''WesternAnimation/SpongeBobSquarePants''
** In one episode, the "superheroes" lost control of their powers and were badly injured, and Mermaid Man was too weak to fight. However, Barnacle Boy (who just had a FaceHeelTurn and called himself "Barnacle Man") decides to simply go back to being good, just because he can now have an adult-sized Krabby Patty. The other villains are later seen in jail, participating in the EverybodyLaughsEnding.
** TheMovie has Plankton actually succeed in stealing the Krabby Patty formula (though, natch, [[TheUnreveal he doesn't read it to us]]).
** In "Wishing You Well" he also gets his wish of growing to several hundred feet to "crush his enemies". His appearance ends with him happily knocking down random buildings in Bikini Bottom.
* Designated villains The Really Rottens actually won in at two episodes of the ''[[WesternAnimation/LaffALympics Laff-a-Lympics]]''. Usually most of their points were ruled invalid by the judges, but yep, a couple of times, the rotten bastards won. (And in another episode, the end result was a three-way tie, because the Rottens were awarded bonus points for breaking a world record during one event.) Note that the one time they won legitimately, they didn't like it at ''all''. Apparently it's not a victory for them unless they won by cheating. An issue of the ComicBookAdaptation (Marvel #5) had the Rottens apparently renouncing their cheating ways and winding up winning. However, they were disqualified because The Great Fondoo and Magic Rabbit, who were "kicked off" the team, kidnapped Boo Boo Bear and Blue Falcon, took their physical forms through Fondoo's magic, and caused the Yogis and Scoobys to lose on purpose.
* On a similar subject, one episode of ''WesternAnimation/WackyRaces'' actually ends with Dick Dastardly placing in first. But unlike the Really Rottens' example, he doesn't get to keep his victory, because the announcer then shows a slow-motion replay of the race's finish that shows that the Mean Machine stretched its front forward to give the illusion that he came in first (despite the fact that if you look at the actual finish, you don't see such a thing happening, meaning the judges may have doctored the footage to screw over Dastardly out of bias). Watch the clip [[http://www.youtube.com/watch?v=AZv8HdAS8Vk here]].
** See the scenes following it. The Mean Machine's nose was in its extended state and it ends with Dastardly cursing his disqualification. Chalk it up to LazyArtist.
** Dastardly actually won two races outright in the comic books: "The Scavenger Scramble" (Gold Key #7) and "Trek To Tazmania" (Archie Comics #1). There were catches to the victories, however. Hanna-Barbera Fun-In (Gold Key #5) had a one-pager of Dastardly pushing the Mean Machine across the finish line after Muttley bails on him, and he uses the trophy, filled with hot water, to soak his feet.
* In an episode of ''WesternAnimation/XiaolinShowdown'' in which Omi freezes himself so he can find his future self (doesn't work of course because ''he wasn't there'') he ends up in a BadFuture where Jack Spicer has taken over the world. The crazy part is that he apparently defeated and captured the other three villains, despite them being far more evil and powerful.
** On a lighter note, he also won in two episodes, one where the robot he sent lost the showdown, but he stole all the monk's Sheng Gong Wu (in the "shake the heroes out of their comfort zone" model), and another where Omi actually loses due to misusing a shen gong wu, and the episode has a downer ending. Despite being an IneffectualSympatheticVillain, hes had several {{Near Villain Victor|y}}ies as well.
* ''WesternAnimation/LooneyTunes''
** One short (the made-for-TV short "Soup Or Sonic") has [[WesternAnimation/WileECoyoteAndTheRoadrunner Wile E. Coyote catching the Roadrunner]]. Of course, the coyote has shrunk down to a comically puny size so the Roadrunner is '''much''' bigger than him. Wile E. [[LampshadeHanging lampshades this by]] [[NoFourthWall pointing out to the audience that he has absolutely no clue what to do next.]]
--->'''Wile E. Coyote:''' [[TalkingWithSigns (Holds up a sign)]] Okay, wise guys, you always wanted me to catch him. Now what do I do?
** Also, in Creator/CartoonNetwork's ''IShouldntBeAlive'' [[http://vimeo.com/11486841 short on the Coyote]], after spending almost a whole year attempting to attack and capture the Road Runner, he finally has him within his grasp (he simply laid out some bird seed and leapt at him while he was eating), only to discover that his finger muscles were too weak to do anything to him.
** A bumper on ''The Road Runner Show'' (CBS, 1966-68; ABC, 1971-72) had the coyote diverting the Road Runner's attention by drawing a portrait of the two, the coyote in the drawing with a rifle in hand. The coyote grabs the Road Runner's neck only to have the coyote drawing blast him in the ass with the rifle.
** Also Elmer Fudd defeated Bugs at his own game in ''Rabbit Rampage'' (a semi remake of ''WesternAnimation/DuckAmuck'') as well as in ''Hare Brush'' (albeit due to something of a personality exchange, with an insane Elmer "turning" into Bugs). He also finally "killed da wabbit" in ''WesternAnimation/WhatsOperaDoc'' ([[MyGodWhatHaveIDone though didn't really find victory all that satisfying]]). Two other cartoons, Fresh Hare and Bugs' Bonnets, ended in a draw.
** In the original nine-minute long version of ''Duck Dodgers and The Return of the 24th and a Half Century'' Marvin the Martian seemingly achieves his goal of detonating the earth. With Dodgers distracted from his duties and earth's destruction almost certain, Marvin is left with no choice but to ensure the viewers "it's only a cartoon". Oddly this was cut from the shortened theatrical version of the short, though since it ends with Dodgers still having not stopped Marvin, the implication is still there.
** Even following his Flanderization into a ButtMonkey, WesternAnimation/{{Daffy|Duck}} seemed to score more victories than most other fall-guys in the series, [[spoiler: knocking out Taz in a CurbstompBattle in ''Ducking The Devil'', being the first foe to defeat Speedy Gonzales in ''Mucho Locos'' to name a few. Counting an [[http://www.youtube.com/watch?v=5RIvO74ZC5c obscure Tang endorsement from ''The Bugs Bunny Show'']] and Creator/CartoonNetwork's [[http://www.youtube.com/watch?v=WpjVBeDalTY Big Game from 2001]], he has also defeated Bugs twice as well.]] Also, perhaps due to being created by fans of the shorts and the character, some later features tend to [[ThrowTheDogABone throw Daffy a bone]] a few times as well.
* Almost happens in ''WesternAnimation/AdventuresOfSonicTheHedgehog''. When the normally incompetent [[GoldfishPoopGang Scratch and Grounder]] are converted into [[NinjaPirateZombieRobot ninja robots]], they almost manage to kill Franchise/{{Sonic|TheHedgehog}} and Tails; if it wasn't for Sonic and Tails escaping via sheer luck.
** In the Chaos Emerald four parter, Robotnik manages to outsmart or overpower Sonic on four consecutive occasions to claim all four Chaos Emeralds and transform into the "Supreme High Robotnik, MASTER OF THE UNIVERSE!" He handily defeats Sonic in their first bout, after which the heroes rely on a TemporalParadox to defeat him.
* The ''WesternAnimation/SuperMarioWorld'' episode has Bowser actually make off with the money he made selling his mutant food to the cavepeople (or at least two bags of it), with Mario and Peach making no effort to stop him ([[VillainExitStageLeft not that they ever tried before, though]]). Perhaps it has something to do with the fact that his restaurant actually was a legal business, even though he was using it to turn the cavepeople into his {{Mooks}}.
** He also kept the money when he sold televisions to the cavepeople. In the cartoons, [[CutLexLuthorACheck someone cut Bowser a check]] and he's been abusing it ever since.
** ''WesternAnimation/TheAdventuresOfSuperMarioBros3'' episode "Crimes R Us:" In spite of their massive failure to rob the Mushroom Kingdom Treasury, Koopa and the Koopa Kids do manage to get away with over 1,000 items stolen from the Mushroom citizens.
** In ''Series/TheSuperMarioBrosSuperShow'' episode "Flatbush Koopa," Bowser is attacking Brooklyn, and Mario succeeds in trapping him back in the Mushroom Kingdom. Only he realizes too late that he's trapped there too, and the episode ends with Bowser blasting away at Mario and the gang, who are running away.
* In an episode of ''WesternAnimation/JusticeLeague'', a group of Superman villains teamed up, planning to use their combined talents to finally kill the big blue alien once and for all. Naturally, the Justice League wipe the floor with them before Superman even gets there, but they still manage to pull it off! The one who made the killing blow? ..... Toyman. [[spoiler: Yeah, it was Toyman in a HumongousMecha and Superman was really only sent thousands of years into the future and returned home at the end of the episode, but still. Toyman.]]
* Possibly the only ''WesternAnimation/TomAndJerry'' cartoon where Tom doesn't get utterly humiliated at the end by Jerry, ''Southbound Duckling'' ends with Tom successfully trapping both Jerry and the Duck.
** Tom wins in a total of 13 different cartoons including ''Million Dollar Cat, The Vanishing Duck'' and ''Duel Personality.''
** He continues this tendency in ''WesternAnimation/TomAndJerryTales'', where at least half a dozen episodes end on him getting the last laugh on Jerry.
* This pattern was replicated with Hanna-Barbera's later cat and mouse team ''Pixie And Dixie and Mr Jinks'' in ''WesternAnimation/TheHuckleberryHoundShow''. Perhaps due to his even more ineffectual qualities, Jinks actually came out on top a fair bit more often than Tom.
* In the ''WesternAnimation/KimPossibleMovieSoTheDrama'' (the original GrandFinale), Dr. Drakken finally works out a way to beat Kim Possible and to overrun the world at the same time. It's only thanks to Ron's LoveConfession that she finds back her HeroicResolve.
* ''WesternAnimation/InvaderZim'' has nearly succeeded in taking over the world/defeating [[HeroAntagonist Dib]] several times, only to be beaten by one DeusExMachina or another. However, there ''is'' one time he ''did'' win: in "Bad, Bad, Rubber Piggies", he uses a time machine to repeatedly cripple Dib in the past until he dies in the present. To repeat - Dib, the only person standing in the way of Zim's plans of WorldDomination, is ''dead''. Of course, then the ButterflyOfDoom kicks in, and Zim is forced to hit the ResetButton, returning Dib to normal. Which really wasn't a win; Dib only died for a split second, and once he came back he was actually a greater threat than ever, almost killing ''Zim'' before he quickly hit the ResetButton. Neither Zim nor Dib ever gets a complete win, of course, but Zim does better than Dib fairly often.
** Although he didn't actually successfully complete his plot, Zim does get one satisfactory ending in which Dib is left trapped inside a cage with a vicious monkey while Zim gets to watch. Likewise, another episode in which it is revealed that Zim is allergic to water ends with Zim unleashing a monstrous water balloon filled with the city's water supply FROM SPACE directly onto the Skool and Dib. Finally, although it was a trivial victory, Zim fooled Dib into believing that he was granted special powers by shoe ghosts that allowed him to single-handedly take down Zim and the entire Irken armada. It ends with Zim revealing that he in fact had Dib under a simulation in a successful attempt to prove that Dib had thrown a muffin at him the day before. Although Zim never truly wins, he has been known to achieve multiple moral victories in the name of the Irken Empire.
* ''WesternAnimation/PhineasAndFerb'':
** In one episode Candace actually does succeed in busting her brothers, leading to Phineas and Ferb being sent to military school. [[spoiler: However, this turned out to be AllJustADream, which also turns out to be another dream Perry has in which Candace unintentionally blows his cover.]]
** We get a twofer when a time travel episode had her future self come back and bust them, causing a bad future where Dr. Doofenshmirtz rules. [[ResetButton Of course, it gets fixed.]]
*** Present Candace also busts them in the future, when she reveals to her mother everything Phineas and Ferb had done. However, Phineas and Ferb are now adults, and their mother can no longer punish them.
** Candace also succeeds in busting the boys in "She's the Mayor" where it goes so far as Mom actually berates them. Unfortunately for Candace, time rewinds at that point, but admit it, this ''is'' the closest she's ever gotten.
* ''Anime/TransformersCybertron'' episode 25, "Retreat": [[TheStarscream Starscream]] pulls a {{Determinator}} on the Autobots, managing to steal the Omega Lock and the three Cyber Planet Keys found thus far. This after ''successfully'' betraying Megatron. He goes on to [[MakeMyMonsterGrow supersize himself]] and become a major threat on his own until towards the end, and his showdown with Galvatron.
** The ''original'' ''[[WesternAnimation/TheTransformers Transformers]]'' had "Revenge of Bruticus" where the Autobots and Decepticons [[EnemyMine team up]] to defeat Bruticus, who is apparently destroyed...except after the Autobots have gone, it is revealed that Megatron faked his destruction and has actually reprogrammed him to serve the Decepticons.
** The episode preceding that is an even more powerful example."War Dawn", featuring the creation of the Combaticons by Starscream, showcased the Decepticon exile successfully defeat a handful of top Autobots, taking their energy chips for his new militia, as well as those of Decepticon warriors Dirge and Ramjet. The episode reaches its zenith with the Combaticons merging into the super warrior Bruticus, who cleanly defeats Constructicon gestalt Devastator before capturing Decepticon leader Megatron himself. With Megatron trapped in Bruticus' death grip, Starscream actually forces his former commander to surrender, and this all-but-actual defeat is only thwarted by the timely arrival of yet another Decepticon gestalt, Menasor, who drops the Combaticon combiner with one sucker punch.
* ''WesternAnimation/ReBoot'':
** {{Defied|Trope}} in season 3: Hack and Slash ''would have'' succeeded in executing Cyris, but Slash refused to go through with it. It turns out Slash never wanted to win in the first place, counting on (now-absent) Bob to prevent him and Hack from doing anything ''too'' bad.
** There is also "Megabyte's Bane" at the end of season three. To quote:
--->'''Megabyte:''' No, you remember boy! How I turned defeat into victory... how I left you with a ''dying'' system...\\
'''Mouse:''' One last double-cross, sugah? ''[turns Megabyte's portal into a port to the web]''
::: He would have won, too, if it weren't for the timely lost-game that forced the system to, well, reboot.
** Played straight in season four, which ends on the mother of all cliffhangers, with Megabyte in control of the Principal Office.
** This happened in a few episodes of season 1, with Megabyte's plans succeeding at first until Bob & co manage to save the day. Hexadecimal came the closest, actually, in the episode 'Medusa Bug'. Bob was the only one immune to the bug because of his Guardian status, but everyone and everything else in Mainframe got turned to stone. Then he pointed out to Hex that she had just brought complete and total ''order'' to the entire system. Needless to say, she was disgusted, and immediately reversed the effects of the bug.
** Not to mention the end of season two, where Bob and Megabyte end up in an EnemyMine situation, trying to save Mainframe from being devoured by the web. Naturally, once the immediate danger to the system was under control, Megabyte double-crossed Bob, shooting him into the web. (Bob survived because of his Guardian code, but no one would know this for sure until late in season three.)
** In the middle of season three, the User manages to defeat Enzo and win the game. (The only reason he, [=AndrAIa=], and Frisket weren't nullified is because they were able to convert to gamesprite mode.) Matrix got his payback towards the end of the season when the Users wound up in Mainframe thanks to the system's instabilities.
* In the [[WesternAnimation/MegaMan Ruby-Spears Mega Man cartoon]], while his primary goal wasn't achieved, Wily made off with the money from robbing the citizens in "Crime of the Century" and the money from selling a shrunken Washington D.C. in "The Incredible Shrinking Megaman". If you want to get technical, he also got all the money from selling Fun World tickets.
* In ''WesternAnimation/TheDreamstone'' episode "Argorrible Attack", the Urpneys actually succeed in giving the majority of the Land of Dreams nightmares ([[PokeThePoodle a small time victory]], but exactly what Zordrak wanted). The heroes try to give Viltheed good dreams in revenge, and it actually proves somewhat ineffective. Though granted after that they decide to just [[CurbstompBattle beat the crap out of all of them]] instead.
** They do this again in "The Dream Beam Invasion", shrinking into the Noop's dreams and sabotaging them for one night. While they are foiled the following attempt, Frizz and Nug still manage to sneak into a dream and succeed. An angry Rufus, Amberley and Albert shrink into the dream seeking retribution, but [[MilesGloriosus change their mind]] when the Urpneys start growing back inside the dream, allowing them to retreat ([[AmusingInjuries albeit just above a lake...]]).
** Also in "The Spidermobile" Blob and his gang effortlessly overpower the entire Wut army and capture the Dreamstone (along with Rufus, Amberley and Pildit) using the aforementioned machine. For once they do not screw things up, it is [[NiceJobFixingItVillain Zordrak and Urpgor instead that lose the stone]], something Frizz and Nug find to be ActuallyPrettyFunny.
** Zordrak also succeeds in sending nightmares in the pilot and "The Nightmare Stone", while Zarag manages to do so in "The Substitute". It is also implied Argorribles actually make their way past the stone's barrier and succeed in giving nightmares on a frequent basis, just in ''very'' few numbers.
* Four ''WesternAnimation/{{Popeye}}'' cartoons have Bluto/Brutus winning, but it is all precipitated by Popeye himself:
** In ''Hospitaliky'' (1937) and ''For Better Or Nurse'' (1945), Popeye and Bluto are both jockeying to severely injure themselves so they can get close to nurse Olive at the hospital. Popeye ends up force-feeding his spinach to Bluto, who delivers the necessary punishment to send Popeye to the hospital. ''I Bin Sculped'' (1961) has Popeye and Brutus vying to be Olive's model for a statue depicting a tired, beat-up specimen. Again, Popeye gives Brutus his spinach. He does so again in ''Round the World in 80 Days'' (1960) as a means to win a global race (Brutus socks Popeye on the chin and it sends Popeye circumnavigating the globe to the race's finish).
--->'''Bluto:''' ''[after he and Popeye both miss getting hit by a train]'' Ya runt! Now neither one of us is goin' to the hospital!\\
'''Popeye:''' Oh, yeah? Well, ''one'' of us is goin' to the hospital... ''[takes out spinach]'' and it '''''ain't you!!'''''
** Brutus (Bluto's name in the 1960s) actually comes up smelling like a rose at the end of ''The Day the Ball Went Over'' (1960) without even laying a finger on Popeye, whose nitroglycerine-laced ping-pong ball explodes on him when he intends to have it explode on Brutus.
--->'''Olive:''' Is there anything special you'd like, Popeye?\\
'''Popeye:''' Yeah... [[MediumAwareness a new writer to writes me spinach back in the script!]]
* The ''WesternAnimation/JakeAndTheNeverLandPirates'' hour-long special "Jake Saves Bucky" has Captain Hook challenging the protagonists to a race for ownership of the Buccaneer. He actually wins, only to lose it in the second half because a loophole in their contract that he didn't want to show them allowed them to reclaim it if they completed a certain task by sunrise.
* The ''WesternAnimation/{{Jem}}'' episode, "The Day The Music Died" has the Misfits taking over what's left of The Holograms and The Stingers after Riot tricks Jem into taking a cruise with him to Mexico and then becoming stranded on an island. Once Jem is found and returns home, Pizzazz quickly gives control of Starlight Music back to Jerrica/Jem without a fight because all the money she made in her absence went right back into taking care of the Starlight Girls and maintaining Starlight House.
* Peg Leg Pete did win one bout against Mickey in the ''WesternAnimation/ClassicDisneyShorts''. "The Barn Dance" ends with him winning Minnie's affections after being unimpressed by Mickey's poor dancing skills. The mouse is in tears.
* ''WesternAnimation/MyLittlePonyFriendshipIsMagic'':
** Minor antagonist [[StageMagician Trixie]] returns to Ponyville (under the influence of an ArtifactOfDoom) and uses said artifact's power to defeat Twilight Sparkle and successfully banish her from Ponyville. As you can imagine, her victory (and quasi-military occupation of Ponyville) does not last long, but still, she did defeat [[TheArchmage Twilight Sparkle]].
** Another episode pits adventurer Daring Do against Dr. Caballeron, who plans on selling a stolen ring to Ahuizotl. Daring Do disguises herself as an elderly adventurer and tries buying it from him, but Ahuizotl appears before they can make the trade. Dr. Caballeron gives Ahuizotl the ring and with Daring Do distracted he makes off her sack of bits, accomplishing his mission and then some.
* In the ''WesternAnimation/ClassicDisneyShorts'', WesternAnimation/DonaldDuck normally loses when confronted with Chip 'n' Dale, despite the fact that they are typically the aggressors in the mess. In the short "Working for Peanuts", Donald actually manages to repeatedly thwart them, with the aide of Dolores the Elephant. Averted, though, in that they ''still'' end up getting what they wanted, by successfully faking a place for themselves in the zoo as rare albino chipmunks.
* A few episodes of ''WesternAnimation/JimmyTwoShoes'' end with [[TheCaligula Lucius]] having the upper hand, including "The Product Tester" and "Catalog of Misery".
* A recurring trope with any show written by Creator/GregWeisman. Being the guy who created that [[XanatosGambit Xanatos]], it's quite common for the heroes to succeed only for the viewer to realize that the villain's plans never hinged on the outcome of the heroes' intervention. A good example from WesternAnimation/{{Gargoyles}}. Xanatos orchestrated the jail break of the Pack (except Fox, who decided to stay) with some covert tactics and a robotic duplicate that allowed him to claim no involvement and then gives them upgrades to boost their ability to fight the Gargoyles. Of course, the Gargoyles foil the escape and manage to get the improved Pack Neutralized, but the threat to the the Gargoyles was incidental. Xanatos couldn't care less if they had won or lost, as the goal of this scheme was to create a mass jail break that Fox would refuse to partake in, thus securing her an early release from an impressed parole board.
* ''WesternAnimation/XMenEvolution'': The Brotherhood boys pretty much always get their asses kicked by the X-Men, however, in the season 1 two part finale, they actually manage to defeat them (along with Rogue defeating Toad). And an episode in season 2 depicts a fight between the two groups in a mall at night; as usual, the X-Men seem to have won again, but then Wanda Maximoff shows up...
---> '''Blob:''' All right! We finally beat 'em!
* The very first episode of Season 3 of ''WesternAnimation/HeManAndTheMastersOfTheUniverse(2002)'' ended with the evil forces of Skeletor actually defeating He-Man and his allies in clean battle. Granted, the fight was precipitated by the Masters going to Snake Mountain only to warn Skeletor of the impending danger of an even greater evil (King Hsss, ruler of the mythical Snakemen) about to escape the bowels of Snake Mountain, but when the battle was fully engaged and the Masters were resigned to defending themselves, the Evil Warriors definitely had their number. Stinkor took out Mekaneck, Tri-Klops defeated Man-At-Arms, Whiplash (with help from Mer-Man) beat Stratos, and Skeletor and Evil-Lyn together managed to deliver He-Man himself one of the extremely rare losses by knockout he would ever suffer in the series. Skeletor tops it off by taunting the routed Masters with "See how they run: the Masters of FAILURE!!!" Of course, the immediate and foretold Rise of the Snakemen would make this a decidedly PyrrhicVictory....