Despite many fans enjoying their time with Ash and the various circumstances he finds himself in alongside newly introduced companions, many people tune in to see how he fends off against opponents who wish to test Ash's skills.
Whether the person is a rival or a one-time character, Ash has been through many battles that required him to think about the commands he gave to his Pokémon. Although many have their gripes with how some of the battle's conclusions turned out, many of Ash's bouts will forever remain inside fans' minds.
10 Drake Was Someone Who Felt No One Could Defeat Him & His Dragonite Until He Encountered Ash & His Pokémon Team
Although the Orange Archipelago wasn't an official region in the mainline Pokémon games, Ash endured many great Orange Island Pokémon battles during his exploration. One of these battles featured him going up against the toughest Orange Archipelago Pokémon trainer, Drake, who felt no one could defeat him and his Dragonite, until he met Ash.
Drake put Ash through an intense bout, and his Dragonite managed to take down Charizard, one of Ash's best Pokémon he had at the time. However, Ash didn't give up and relied on his Pikachu to deliver the electrifying shock of a lifetime to Dragonite, which secured Ash the victory.
9 Diantha Is Kalos' Pokemon Champion Who Gave Ash A Great Battle Despite Losing To Him
Despite Ash having many shortcomings concerning his loss ratio in Pokémon leagues, Ash has claimed victory over many, even Pokémon trainers Ash shouldn't be able to defeat. Diantha, Kalos's Pokémon champion, was one of these characters whose Mega Gardevoir was unable to withstand the might of Ash's Greninja.
Despite being interrupted by Team Rocket and being a Pokémon battle that consisted of both trainers utilizing one Pokémon each, it was a spectacle to behold via its gorgeous animation and intensity. Although Ash's later losses in this Pokémon season will make fans ponder his skills, battling a region's champion is no easy task.
8 Sawyer Is A Pokémon Trainer That Bonded With Ash & Gave Him An Intense Pokémon League Battle From Start To Finish
Regarding Ash's many adventures in each Pokémon region, his relationship with Sawyer is one that some people could respect because of how both trainers built off and grew alongside each other. Sawyer was a Pokémon trainer that made fans feel like Ash met his match.
Despite giving Ash a run for his money, Sawyer's Sceptile couldn't withstand Ash's beloved Greninja, who managed to secure Ash a win over Sawyer. Although Ash came away from the Pokémon battle as the victor, it was a battle that required him to really think about the orders he wanted his Pokémon team to follow.
7 Paul Is One Of Ash's Greatest Rivals That Always Challenged Him To Step His Game Up Whenever They Battled Each Other
Paul was a Pokémon trainer many fans adored and despised because of his approach toward Pokémon relationships, training, and battling that conflicted with Ash's morals. Despite being the series's protagonist, Ash lost to his rivals many times before finally securing a victory over them, and Paul was one of them.
Although Paul was a trainer that loved mocking Ash's battling styles and knowledge of the sport, he'd soon meet his downfall in the Sinnoh region's Pokémon league when Ash's Infernape defeats his Electivire with an intense Flair Blitz, granting Ash the victory.
6 Flint Is One Of Sinnoh's Elite Four Members Who Defeats Ash & Reignites Volkner's Passion For Pokémon Battling
Flint is one of the strongest elite four members in the anime and someone who gave Ash a fierce battle to show his old friend Volkner why he's worth battling. Volkner was Sunyshore City's Gym Leader, who became more attached to technology than Pokémon battling to the point where he had a robot installed to give people free gym badges.
Although Flint defeats Ash, he makes sure Volkner witnesses Ash's impressive skills in hopes he can convince Volkner that Pokémon battling is still a fun sport. As expected, Flint's battle with Ash entices Volkner to give Ash an intense battle fit for a Gym Leader.
5 Gary Oak Was Ash's Childhood Rival Who Always Knacked On Him & His Team
Before exploring other regions, Ash always had a bitter rivalry with Gary Oak. Despite being someone who liked bragging about his team, Gary wasn't a pushover and managed to put Ash in his place many times in the anime from beginning to end.
Whether it be showing off his outrageous amount of gym badges, Gary made sure Ash was second fiddle. Although Gary proved to be a difficult opponent to triumph over, Ash managed to defeat him during their bout in the Johto League's Silver Conference, thanks to his Charizard.
4 Leon Is The Galar Region's Pokémon Champion That Gave Ash An Intense Champion Vs. Champion Pokémon Battle
Leon is a newly introduced character in the Pokémon franchise and serves as the Galar Region's Pokémon champion. Not only was he featured in the games, but he's also made an appearance in Pokémon Twilight Wings' best episode titled "Sky." Not only that, but Leon made sure to grant Ash a champion vs. champion Pokémon battle he'll remember.
Although Ash was a novice to Dynamaxing and Gigantamaxing, Leon made sure to explain the mechanics to him before their Pokémon battle. Although Ash's Pikachu put up an intriguing fight against Leon's Charizard, Leon walked away as the winner.
3 Professor Kukui Is The Alola Region's Pokémon Professor Who Lost To Ash Despite Having A Legendary Pokémon On His Side
Although many of Ash's battles with legendary Pokémon left him in utter defeat at the hands of their might, his Pokémon battle with Professor Kukui and Tapu Koko changed that notion granting Ash a victory over this region's professor. Although Ash won the match, going against a legendary electric and fairy-type Pokémon like Tapu Koko wasn't easy.
Despite some fans having issues with Ash's victory over Professor Kukui, seeing him and Pikachu hold their own against a Legendary Pokémon was something others adored witnessing. It's a Pokémon battle that'll leave an impact on fans and shows that Ash can triumph over many obstacles.
2 Tobias Is A Notorious Character For Using Over-Powered Pokémon Against Ash During Their Sinnoh League Pokémon Battle
Tobias is a trainer many despise not only for using two insanely powerful Pokémon against Ash but for how he came into the series as a character whose purpose was to prevent Ash from winning the Sinnoh league. Despite fans' grievances and disappointment over Ash's loss against Tobias, his team managed to pull off an outstanding feat.
During their battle, Darkrai defeated many of Ash's Pokémon; it couldn't withstand the might of Ash's Sceptile. Despite giving Ash a victory over a mythical powerful Pokemon, Tobias's Latios makes sure to defend Tobias's honor by defeating the remainder of Ash's team, despite fainting in battle alongside Ash's Pikachu.
1 Alain Defeated Ash In The Lumiose Conference But Learned Valuable Life Lessons From Him
Alain was an opponent that put Ash's skills to the test during the Lumiose Conference and left him defeated despite having a substantial Pokémon team during the Kalos region anime. Despite Ash's loss over Alain, he made sure to give it his all in the battle, as both trainers kept losing Pokémon left and right.
Despite the growth Ash and his Greninja had as teammates, their bond wasn't enough to withstand the might of Alain's Mega Charizard X. The battle concluded with Ash's defeat; the anime acknowledged both trainers left on good terms.