The Pokemon anime may have its differences from the games, but one thing remains an equally definitive aspect between both: battles. Most of the Pokemon anime's characters live and breathe to battle one another, whether it's in Gym battles, League Conference battles, or World Coronation Series battles.
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Of course, battles don't exist on their own in the anime. They come with stakes that exist outside of official standing. Some battles carry real conflict and emotional weight, making for some of the most exciting moments of the entire series. We'll highlight the best of the best when it came to battles that not only kept fans on the edges of their seats but were narratively important for those involved.
Updated November 27, 2022, by Kyle Laurel: The Masters Eight Tournament gave fans a lot to remember. With Ash completing his path to becoming a World Champion, here's an updated list with a few more recent battles you might recognize!
17 Ash vs. Clemont (Lumiose City Gym)
The X&Y anime had quite a few awesome Gym battles (this one won't be the last to make the list), but this one stands out thanks to Clemont being one of Ash's traveling companions. Despite the friendship they had, neither Ash nor Clemont held back as the former fought for the Lumiose City Gym Badge.
It was a close fight throughout, and both showed off their battling styles very well; Clemont was a smart strategist, but not even a bulletproof strategy could break Ash. Goodra would be the battle's MVP for the latter, as it managed to withstand a flurry of hits from Clemont's Luxray before using Bide to blow double the damage back, knocking the latter out to win the match.
16 Ash vs. Lt. Surge (Vermilion City Gym, Second Match)
For how primitive it is compared to its current-day seasons, the Original Series has some pretty memorable Gym battles to its name. While some props should also be given to Ash's fiery battle against Blaine, Ash's rematch against Lt. Surge is arguably the best of that particular crop.
This was Ash's first true victory against a Gym Leader, and the first time Ash's innate determination translated into success. It showed glimpses of the Trainer he would become: one that executed strategies on the fly and worked best with high-agility Pokemon. The same can be said for Pikachu as he beat Lt. Surge's Raichu, establishing his dominance over his evolved form and showing his desire to prove himself as just a Pikachu.
15 May vs. Drew (Kanto Grand Festival)
May's rivalry with Drew is arguably the best one that doesn't involve Ash, and it hit a turning point at the Kanto Grand Festival. May was getting better and better as a coordinator and Drew recognized that. But nothing was proven until they battled under the brightest lights.
While the battle wasn't as visually stunning as contest battles would become later in the series, it was definitely something to watch for its time. It was a close battle all the way until May edged out the victory with Combusken by pulling off a Sky Uppercut to Drew's Absol at the last second. May wouldn't win the whole Festival, losing to Solidad in the semi-finals, but this battle proved she'd finally arrived as a Coordinator.
14 Ash vs. Brandon (Battle Pyramid, Third Match)
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While Ash's first bout against Pyramid King Brandon was a cringe-worthy possession episode, and his second was another disappointment from his Torkoal, his third was both a throwback to the good ol' days and an overall exciting match.
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Ash decided to bring back his old trio of Kanto starters (Charizard, Squirtle, and Bulbasaur) for his Battle Frontier swan song. It didn't start off so hot, losing Charizard early after a fumbled Seismic Toss. However, the rest of the team managed to hold their ground — especially Bulbasaur, who managed to do a lot of dirty work. As icing on the cake (pun not entirely intended), Pikachu won the Brave Symbol for Ash by adding the first Legendary to his hitlist: Brandon's Regice.
13 Alain vs. Ash (Lumiose Conference)
While this was a more honorable way for Ash to bow out of a League than getting wiped out by Tobias in Sinnoh, Ash's Greninja losing to Alain's Charizard had been a point of contention for a while.
Still, Ash's first appearance in a League Final was an absolute Blast Burn of a bout from start to finish. Even though he ultimately lost, Ash proved he belonged, having been the only Trainer in that tournament to put up a good fight against Alain, who finally found the joy that came with battling someone in his ballpark. Good thing, too, because chances for a potential rematch were dashed by Alain blowing it in the Masters Eight Tournament.
12 Ash vs. Gladion (Manalo Conference)
The result of this battle was such a monumental moment that it's currently the basis of a real-world holiday, but the whole battle itself was worth remembering as well. While the Alola League Final wasn't the six-on-six battle you see in most League tournaments, it was a culmination of one of the better rivalries in the series, and it was certainly all killer, no filler.
It featured a clash of two Legendary-tier Pokemon in Ash's Melmetal and Gladion's Silvally, an explosive draw between Pikachu and Gladion's Zoroark, and the final battle between two formes of Lycanroc. As many probably know, Ash's Dusk Lycanroc won in the end, finally giving Ash the League trophy that had eluded him for decades.
11 Ash vs. Korrina (Shalour City Gym)
Ash and Korrina have faced off a few times, and while their World Coronation Series rematch was also exciting, their first bout at Korrina's Gym was a sight to behold. This battle was a benchmark in Ash's ongoing history with Lucario, as he witnessed its Mega Evolution at the true extent of its powers.
Pikachu had the tough task of battling against Mega Lucario after it knocked out Ash's Hawlucha and Fletchinder in convincing fashion, but after a close blow-for-blow affair, Pikachu won. Aside from it being one of the more important Gym battles in the whole series, it was also one of the X&Y season's many visual achievements; almost every frame of the battle showcased some stunning animation.
10 Ash vs. Drake (Orange League)
Fans might not count the Orange League as a real League, or at least as important as, say, the Alola League. But it can't be denied that Ash's final battle there against Supreme Gym Leader Drake was spectacular to watch.
A huge reason for that was Drake's ace, Dragonite. It wasn't just any other pseudo-Legendary; it had ten moves in its arsenal and managed to beat three of Ash's other Pokemon. Leave it to Pikachu to finish the job, though, as he stood his ground and managed to beat it with a point-blank Thunder to the head, giving Ash the victory and a spot in the Orange League Hall of Fame. Not bad for his first full six-on-six battle ever.
9 Ash vs. Maylene (Veilstone City Gym, Third Match)
Fans like to look at this battle as the first one that truly had high-quality action animation, and rightfully so. The momentum never swung too far in one direction, as both Ash and Veilstone Gym Leader Maylene did everything they could to stay on their feet. Ash showed particularly good patience when it came to switching out Pokemon as necessary.
In the end, it came down to Maylene's Lucario and Ash's Buizel, and the action was non-stop from that point. The two kept canceling each other's power out, even as the roof literally blew off and Buizel's Speed increased in the rain, and it came down to the final Force Palm and Aqua Jet collision. The fight may have ended in a draw, but Ash certainly earned his Gym Badge.
8 Ash vs. Olympia (Anistar City Gym)
Arguably the X&Y Gym battle prototype at its best, this bout between Ash and Olympia, the Gym Leader of Anistar City, was absolute visual candy and then some. In arguably the anime's greatest ever double battle, Ash's Frogadier and Talonflame and Olympia's two Meowstic put on a show, taking advantage of the beautiful Gym and pushing the anime's animation capabilities to its absolute limits.
Amidst all the strategic juggling and unbreakable teamwork from both sides, making for an entertaining battle all on its own, the highlight of the match had to be towards the end. Frogadier managed to create a gigantic Water Pulse through paralysis and Meowstic's Psyshock, causing Olympia to literally foreshadow the Ash-Greninja form it would later evolve into.
7 Ash vs. Iris (World Coronation Series)
Ash's World Coronation Series battle against Iris was long overdue, and though they didn't meet in the Masters Eight Tournament with Iris losing to Cynthia, what fans did get prior was more than enough. Seeing how Ash's former traveling companion transformed from an immature brat to Champion of Unova was fulfilling, to say the least.
The battle itself was memorable in all the right ways, with some of the highlights being the showdown between Ash's and Iris's Dragonite, Ash's Dracovish getting its feet wet, and Iris's Axew being revealed to have evolved into a Haxorus. With all that said, Ash was this battle's victor, with his Dragonite connecting with Iris through her clairvoyance with Dragon-types and pulling off an impressive impromptu Draco Meteor. This was one of Ash's more important battles in Pokemon Journeys, pushing him to the Ultra Class.
6 Ash vs. Sawyer (Lumiose Conference)
The "passionate Ash versus analytical [insert name here]" type of rivalry is a beaten-up warhorse at this point, but Sawyer is that trope put to excellent use. It helps that Sawyer was the first person to really admire Ash as a Trainer.
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That entire narrative made for an excellent Kalos League semi-final, with both sides cooking up strategies on the fly for most of the battle. It ultimately came down to Ash-Greninja and Sawyer's Mega Sceptile, and despite the massive type disadvantage, Greninja would win the match just by the skin of its teeth. Sawyer was undeniably one of Ash's best rivals from a skill standpoint, and this battle was an excellent way to cap off the rivalry for the meantime.
5 Ash vs. Cynthia (Masters Eight Tournament)
This three-episode slog was a decade in the making, and Cynthia immediately confirmed she was no slouch, quickly dispatching Ash's Dragonite, Gengar, and Pikachu. Cynthia also kept Ash on his toes by opting to Dynamax Togekiss instead of Mega Evolving Garchomp, proving that high-class Trainers are as unpredictable as they are dominant.
Ash's remaining Pokemon put in a ton of work, though; Dracovish and Sirfetch'd proved their status as unsung workhorses and set the table beautifully for Mega Lucario. That final showdown against mighty Garchomp consisted of old-school hand-to-hand fisticuffing and was suspenseful right to the very end. Both Pokemon dropped, but Lucario managed to get up, finishing off Ash's comeback effort by the narrowest of margins and literally prompting Cynthia to put off retiring from battling. Absolutely inspirational.
4 Ash vs. Gary (Silver Conference)
Of course, Ash's first rival is still one of his most iconic, and their battle in the Silver Conference is, too. This was a high-octane battle as Pokemon on both sides went down left and right. Gary's strategies were overwhelming at first, but Ash showed just enough mental toughness to scrap out an even fight. The Pokemon continued to drop until only two were left: Ash's Charizard and Gary's Blastoise.
Ash managed to win that iconic face-off despite the type disadvantage, overcoming his biggest hurdle up to that point and proving himself a worthy and even skilled Pokemon Trainer. Meanwhile, Gary humbled himself after the loss as he gained a newfound respect for his rival.
3 Ash vs. Kukui (Manalo Conference)
While it wasn't an official match, the four-episode, six-on-six exhibition match between Ash, Champion of Alola, and Professor Kukui, the ever-popular man behind the Masked Royal, was an instant classic, as both sides showed off their teams' abilities with aplomb.
Just when fans thought the battle had reached its apex after an amazing Torracat vs. Incineroar matchup that led to Torracat evolving, Tapu Koko came down to the stadium and asked to join Kukui's side. It would later call the other Guardians to recharge both sides' Z-Rings, culminating in a Z-Move showdown like no other: Tapu Koko's Guardian of Alola vs. Pikachu's 10,000,000 Volt Thunderbolt. Ultimately, one of the coolest Pokemon battles ever ended with Ash as the victor.
2 Ash vs. Paul (Lily Of The Valley Conference)
This battle wasn't as much of a showstopper as Ash's championship-winning battles, but it carries all its weight with no frills. This was a moral battle that pit diametrically-opposed training philosophies against one another. While Ash was warm and nurturing, Paul was harsh and borderline abusive, and that style wasn't for everybody. It certainly wasn't for the Chimchar he released.
That Chimchar would join Ash's team and evolve into an Infernape, and it would be the connecting string in this three-episode chess match. The battle was neck-and-neck the whole way, and Infernape and Paul's Electivire were the last two standing. Infernape showed Paul what he missed out on as it utilized its formidable Blaze ability and scored the win. This battle most definitely changed Paul for the better, as shown by his character progression long afterward in Journeys.
1 Ash vs. Leon (Masters Eight Tournament)
Good God, what didn't this battle have? Both teams managed to show their chops. Absolutely exhilarating animation. Tons of twists, turns, and callbacks. Eternatus showed up and gave both teams an extra Dynamax. All of Ash's friends were watching!
Everything beforehand aside, the final showdown between Ash's Pikachu and Leon's Charizard alone warrants a top spot here. Ash and Pikachu's entire journey together led up to this, as seen by their unmistakable chemistry on the battlefield, Pikachu's incredible power after years of experience, and Pikachu getting knocked out but finding the determination to get back up and come back way stronger (plus a montage with Ash's old Pokemon!). It's only fitting that it took such a scintillating battle for Ash to officially become the strongest Trainer alive.
NEXT: The Best Duck Pokemon, Ranked
