Ash has faced many tough opponents across his many journeys, from the Gym Leaders such as Brock or Blaine to the champions during the Masters 8 tournament. Despite the challenge, Ash always pushed through alongside his Pokemon and pulled some impressive wins. Conquering the Battle Frontier and becoming the champion of Alola are some achievements he earned through hard-fought battles in thePokemonanime.
Some of these victories are grander than others. Wins that helped Ash grow as a trainer or were the emotional climax of a story arc set themselves apart from other wins the 10-year-old has earned. Let us look back on some of Ash’s best wins throughout history.
10Ash Vs. Lt Surge
While Ash didn’t always earn his gym badges the traditional way during his journey in Kanto, his battle against the Vermillion City gym is one of his most important victories. After a crushing defeat, Ash is offered the chance to evolve his Pikachu into a Raichu. This change would make it strong enough to overcome Surge’s Raichu.
Despite the easy path in front of him, Ash allows Pikachu to choose what it wants to do and sticks to its choice to remain a Pikachu. The two return to Surge and use Pikachu’s superior speed to defeat Surge’s Raichu, proving that any Pokemon can be strong, no matter if it evolves.
9Ash Vs. Nolan
As Ash’s first battle during the Kanto Battle Frontier, Nolan did not disappoint. While the leader of the Battle Factory typically uses a random Pokemon, Nolan decided to use a wild Articuno he befriended to battle Ash’s Charizard. Nolan didn’t make things easy for Ash and Charizard, continuously keeping them on the defensive.
However, after all the training it had done, Ash’s Charizard managed to prove itself and get the win of the icy bird. This victory also marked the first time Ash had everdefeated a Legendary Pokemon, something that would cement Charizard as one of his most reliable partners.
8Ash Vs. Sawyer
Despite starting far behind Ash, Sawyer caught up to the ten-year-old throughout their Kalos journey, to the point that Sawyer managed to defeat Ash and earn all eight badges before he could. This setback shattered Ash’s confidence and briefly caused him and Greninja to split up.
However, this challenge is just what the duo needs to master the Battle Bond and come back stronger. Having their showdown atthe Kalos League competition, Ash acknowledged Sawyer’s skill while taking on his Mega Sceptile. Despite the challenge, he and Greninja reaffirmed themselves as a near-unbeatable team as Ash came out on top, this win leading to Ash’s first time reaching the finals of a Pokemon League.
7Ash Vs. Drake
After losing at the Indigo League, Ash would get a second chance to prove himself when facing the Orange League champion, Drake. While it wasn’t an official tournament, this battle was a great example of how far Ash has come. What makes this battle so memorable is the battle with Drake’s Dragonite.
While none of Ash’s Pokemon individually would be able to defeat it, the team works together to wear it down until Pikachu can get the victory. The cooperation and love between Ash’s Kanto Pokemon made this victory enthralling.
6Ash Vs. Brandon
To become champion of the Battle Frontier, Ash had to defeat Brandon. Having lost to him twice, Ash brought back his core team from Kanto to tackle this latest challenge. Facing Brandon with his Pikachu, Bulbasaur, Charizard, and Squirtle, the ten-year-old fought him with everything he had.
Despite losing Charizard early, Ash proved he no longer needed to rely on the Fire/Flying type as Bulbasaur and Squirtle held their own. The true star was Pikachu, who managed to defeat Brandon’s Regice and make Ash the winner.
5Ash Vs. Gary
Who can forget Gary Oak?Ash’s primary rivalthroughout the Kanto and Johto sagas of the anime, Gary was always ahead of Ash. Despite their long-standing rivalry, the two hadn’t fought each other very often. This changed at the Silver Conference in Johto as Ash and Gary had their first full battle to see which would advance to the top eight of the tournament.
This battle meant a lot to Ash as he spent all night researching Gary’s Pokemon in preparation. His efforts paid off as Ash constructed a team that could win him the match. This fight sees Charizard returns for the first time to defeat Gary’s Blastoise.
4Ash Vs. Paul
Ash’s most brutal rival, Paul, was one of a kind. Paul was Ash’s opposite in every way, seeing no value in training a weak Pokemon to be strong. Instead, he’d catch the Pokemon with the most potential. This difference in opinion brought the two into conflict. A conflict that would have a profound effect on Ash.
This is why their battle at the Sinnoh League and Ash’s victory were so important. This was more than just a battle for Ash — it was a chance to prove that any Pokemon could be capable, no matter what. The connection solidified through Infernape, a Pokemon that once belonged to Paul, now made strong by Ash.
3Ash Vs. Cynthia
A battle several years in the making, Ash’s match against Cynthia was highly anticipated. Ash encountered Cynthia multiple times during his journey in Sinnoh, the two building a mutual respect. So, when it was time for their battle during the Masters 8, the series had a lot to live up to.
These expectations were met as Ash showed severe bouts of ingenuity to keep up with Cynthia’s intelligence. While he started from behind, Ash’s strategies and trust in his Pokemon allowed him to catch up, the battle coming down to Ash’s Lucario versus Cynthia’s Garchomp. Meeting this challenge as well, Ash overcame the odds, advancing to the finals of the tournament.
2Ash Vs. Kukui
While Ash was already the winner of the Alola league, to be crowned the best trainer in Alola, he had one more trainer to conquer. Ash and Professor Kukui had become like father and son throughout the Sun & Moon anime. This bond they formed added that much more emotion to their final battle.
Not only was this Ash’s chance to becomea region’s champion, but he would even receive the opportunity to challenge Tapu Koko. All these loose ends coming together gave this battle emotional stakes that far exceeded Ash’s previous victories.
1Ash Vs. Leon
Ash’s grandest challenge on his journey was Leon, the unbeatable champion of the world. This battle was different than others throughout the anime. It was the culmination of everything Ash and Pikachu had been working towards. Every high and low, every win and loss came down to this moment.
What truly makes this win feel special is that before Ash and Pikachu engage in their final attack, Pikachu sees a vision of all of Ash’s Pokemon cheering him on. Even though they weren’t here, all the hearts the duo touched were pushing them to succeed and reach their dream. As a finale to the Pokemon World Championships, you couldn’t ask for a better victory.
