In all the years the Pokémon anime has existed, Ash may have never won a Pokémon League, but that hasn’t kept the creators from going all out in the battles that took place during it. Each region had some memorable and well-crafted battles (yes, even Unova had one though it was hardly enough to save the whole thing) and this article counts down the best of the best.
5. Ash vs. Tobias
This one is at the bottom of the list because on the one hand, as Team Rocket’s Meowth put, the battle is a “stupid one-sided wipeout.” Tobias was revealed to have entered the Sinnoh League with not one but two legends (and presumably others we never saw) and had a major advantage winning almost every battle with only his Darkrai. On the other hand, even though this battle is very one-sided, Ash proves his mettle by being the only trainer to defeat his Darkrai (even the trainer who made it to the finals failed to do that) and tie with his second Pokemon, Latios.
4. Ash vs. Katie
Katie was a one-off character but still made quite an impression in battle. Her design was heavily based off the adept Cooltrainers from the games and very much embodied the aspect of those trainers in battle. Her use of status moves such as Stun Spore, Disable, and Destiny bond as well as her utilization of type advantages and disadvantages in going on offense, push Ash into a corner during the first half of the battle.
3. Ash vs. Sawyer
This battle was the first time Ash had made it to the semi-finals since Sinnoh and it left many viewers in suspense. Could Ash actually move on to the finals for once? Ash had beaten Sawyer quite a couple times prior to this battle, but it did not stop Sawyer from progressing and he eventually bested his rival. From there onwards, he proved that he was no pushover Despite the battle having two consecutive ties, both trainers pull off surprising strategies in this battle and their prior battles with the pre-evolutions of their respective arsenals were well crafted to lead up to this.
2. Ash vs. Gary
It only took a full generation to have this battle. With that being said, the wait was well worth it. Ash and Gary had only battled once before the Johto League but with just an Eevee, Gary quickly established himself as a force to be reckoned with able to take down Ash’s Pikachu without Eevee being hit once. This battle carried Gary’s strength to the end. From the beginning Gary wastes no time in showing off how much he has learned, as he is able to take down Ash’s Tauros in one blow. The Blastoise he received from his grandfather as a Squirtle when he first started proves to be the powerhouse of his team devastating two of Ash’s Pokemon and neutralizing one. Even the rounds Ash wins in this battle come with Gary doing a great deal of damage. The battle goes back to the roots of Ash and Gary’s rivalry. Gary is often taking a jump ahead and leaves Ash in the dust. But it also proved that Ash finally got onto his rival’s level as of this episode.
1. Ash vs Paul
This battle would have been a lot better had Paul used the same Pokemon he used during the Lake Acuity Battle. They were quite the powerhouses of Paul’s team and ones that were well established since his first appearance. Alas the only Pokemon Paul wound up bringing back to this battle was Electivire. All the others Ash had never battled before this point. The impact of this battle primarily came from the battle at Lake Acuity. All throughout the series Ash had always thought himself as the better trainer with the nice way he treated his Pokemon. While Paul was harsher in his training, he knew how to train his Pokemon well. These methods came full circle in their first full battle at Lake Acuity. Paul not only won that battle but completely crushed Ash only losing two of his Pokemon in the process. And this left Ash devastated as Paul’s tactics proved to be far superior to him and ultimately pushed Ash to do his best. Paul carefully picked his Pokemon and planned his strategies and substitutions far in advance throwing off Ash all throughout the battle. While Paul picked different Pokemon for this battle, his careful planning carried throughout it. He purposefully lets Ash grab an early lead to scout out his team and even takes Ash’s counter-shield strategy and makes it his own. While Ash and Paul had different approaches to being trainers, here they finally battle in the same state of mind and nowhere is this more closely reflected than within the roads of their last Pokemon, Infernape and Electivire. Both trainers and Pokemon realize this and the conclusion of the battle finally gives the two a newfound respect for one another. In a far cry from his usual demeanor, despite losing, he thanks Electivire for a job well done and parts with his rival on good terms. This battle proved to bring a strong rivalry full circle and a send-off to one of Sinnoh’s finest.
Are there any other battles you think deserved a spot on the list? Any you agree or disagree with? Well leave them in the comments below!