The way to be Pokemons world champion was a long one for Ash, littered with earth-shattering losses that had Ash questioning his fitness as a trainer. While Ash lost a lot of times, only a few losses were so devastating that they shook Ash’s confidence right to his core.
Many of Ash’s worst losses were the ones where the most was at stake, such as the Pokémon League championships. Ash worked very hard to earn his gym badges and make it into the tournaments, so losing after coming so close is often a big blow. Other times, it was battles against rivals, or sometimes even gym leaders, that made Ash doubt himself after a substantial loss. The key, however, is that Ash managed to learn from most of the losses, and take the newfound knowledge forward into the future.
10
Ash’s most embarrassing loss was to a recent Snivy
Episode: Pokemon black and white“In the shadow of Zekram!”
Easily one of Ash’s worst losses was his first battle against Tripp, who would go on to become his primary rival throughout his adventures in Unova. Ash met Trip when he was first starting his Pokemon journey, having just picked a snivy from the professor. Trip thought poorly of Ash due to the fact that he was from Kanto, but was eager to fight Pikachu, as Pikachu were not born in Unova. Ash agreed to a battle, but was quickly defeated in one of Pikachu’s most embarrassing losses of all time.
To be fair to Pikachu, he was afflicted with an illness that prevented him from using Electric-type moves, but it still should have taken little more than a single Iron Tail to take down such a fresh and inexperienced Pokemon. This was more of a wake-up call for the audience than Ash, realizing that much of the skills he had previously built up were not going to carry over into Black and white.
9
Ash’s Battle with Tyson Saw Pikachu lose to Meowth
Episodes: Pokemon Ruby and Sapphire“Choose it or lose it!” and “At the end of the day!”
Ash did quite well in the Havergrand Conference in the Hoenn League overall, but his match with Tyson ended up testing his skills. Tyson has a full team of mostly strong Pokemon, such as Metagross, and Tyson was very skilled at using type advantages in a way that Ash never really was.. It was a brutal battle that went back and forth several times, finally coming down to Tyson’s partner, a Meowth in a hat, against Ash’s Pikachu.
While Pikachu should be well versed in battling Meowth at this point, Tyson’s Meowth packs a few surprises, such as the ability to use Thunderbolt. Ultimately, Pikachu collapsed first, costing Ash the win and allowing Tyson to go on and claim the Hoenn League title. Ash was proud of his performance here, but still disappointed to lose after coming so close once again.
8
Ash’s first battle with Lieutenant Serge asked him Pikachu
Episode: Pokemon Indigo League“Electric Shock Showdown”
Ash bravely challenged his third gym, only to find out how woefully unprepared he was when he found himself up against L. Surge’s Raichu, the evolved form of Pikachu. Raichu had much more electrical power than Pikachu could at the time, and defeated him with ease, sending Pikachu to the Pokemon Center, where he was in a relatively serious condition.. Ash began to feel that the only way Pikachu could measure up was to evolve him as well, but Pikachu refused, saying that if he won, it would be as a Pikachu.
Ash respected Pikachu’s wishes, and they finally developed a plan to take advantage of Pikachu’s speed advantage, allowing him to finally claim victory in a rematch. Pikachu’s desire not to evolve would remain constant throughout the series, and Ash wouldn’t really bring up the subject of Pikachu evolving again.
7
Ash’s loss to Paul at Lake Acuity was brutal
Episodes: Pokemon Diamond and Pearl“Step to the metal!” and “Evolving Strategies!”
Paul was Ash’s primary rival throughout Diamond and pearlAnd Paul was a rather cruel and cold-hearted trainer who abandoned his chimchar, which Ash took in. Ash and Paul did not see eye-to-eye on how to catch Pokemon, which eventually led to their heated clash at Lake Akuati in the Sinnoh region. Ash tried to fight tactically, but he couldn’t keep up with Paul’s strategies, being outsmarted at every turn. Paul frequently switches Pokemon and sets up defensive strategies that Ash has no way to counter.
Despite Ash’s Chimchar evolving into Monferno at the end of the battle, it still wasn’t enough, and Ash ended up losing, while Paul still had 4 of his 6 Pokemon able to battle. Ash was seriously depressed after this, but ended up regaining some confidence after fighting off Team Rocket in the next episode.
6
Ash’s battle with Harrison opened up a new world
Episodes: Pokemon Gold and Silver“Playing with fire!” and “Johto Photo Finish!”
From his long-awaited defeat of Gary in the Silver Conference, Ash was next up against Harrison, a trainer visiting Johto from the Hoen region, whom Ash had not heard of. Harrison used Pokemon that Ash was unfamiliar with, such as Kecleon and Blaziken, making it difficult for Ash to know how to counter them.. Despite this, the match went back and forth, and Ash and Harrison were evenly matched. It eventually all came down to Harrison’s Blaze vs. Ash’s Charizard, and despite the type advantage, Charizard lost.
Ash is predictably devastated, having once come this far, but Harrison cheers him up by encouraging him to visit the Hoenn area next. Ash takes Harrison’s advice, setting up the next major series of The Pokemon Anime.
5
Wulfric broke Ash’s trust at a key moment
Episodes: Pokemon XY“All hail the ice battlefield!” and “see the forest for the trees!”
Entering the battle, Ash was already feeling a little hesitant because he had recently lost to his rival Sawyer for the first time, and was not allowed to activate the Bond phenomenon with Greninja during the battle. After, Ash challenged Wulfric for his final Kalos gym badge. Wulfric sends out his Avalugg, which is able to defeat Hawlucha and Talonflame despite a type disadvantage, and finally defeats Greninja, even after Ash triggers the Ash-Greninja formCausing Ash to weaken and the battle to end, having only knocked out one of Wulfric’s Pokemon.
The loss shattered Ash’s confidence so much that he left alone in the forest without any Pokemon with him. Even Serena is unable to get through to him, and Ash runs away again, soon caught in a snowstorm. He finds himself in trouble while trying to help a wild Pokemon, but Greninja appears at the last moment, saving them both. This restores a bit of Ash’s confidence, giving him the strength to try again.
4
Ash’s loss to Alain hurt the most
Episodes: Pokemon XY“Finals not for the faint-hearted!” and “Down to the fiery finish!”
Ash was the closest he ever got to champion status in Kalos, reaching the final round of the Lumiose Conference, where he faced Alan, a rival featured in the Mega Evolution Specials. Ash vs Alan was an intense battle, looking very evenly matched as each knocked out one of the other’s Pokemon in turn. It all came down to Alain’s Mega Charizard X versus Ash’s Greninja in his Ash-Greninja form. With this type advantage on his side, it was Ash’s battle to lose.
Unfortunately, that’s exactly what happened; The clash culminated in a water shuriken and a blast burning, coating the stadium in steam, and when it cleared, it was Greninja who was down for the count. Allen won the championship, and Ash was left with the bitter taste of second place.
3
Ash had no chance against Tobias
Episode: Pokemon Diamond and Pearl“The semi-last front!”
Ash was pretty far into Sinnoh’s Lily of the Valley Conference, putting him in the semi-finals round against a mysterious trainer named Tobias. Tobias’ first Pokemon was a Darkrai, a mythical Pokemon of tremendous power that handily defeated several of Ash’s Pokemon before finally taking it down. Tobias then followed this up with Latios, a legendary Pokemon, which Ash was able to defeat in a simultaneous knock-out with Pikachu. Tobias managed to beat Ash with only two Pokemon, and won the rest of the conference with only Darkrai.
Towards the semi-finals, this was again the closest Ash came to winning it all, but Tobias was simply an impossible obstacle to conquer. Ash’s friends also comforted him with this, and it was an ending that he managed to defeat Darkrai at all, something that no one else in the tournament did.
2
Ash’s Indigo League loss is embarrassing
Episode: Pokemon Indigo League“Friends and Foes Alike”
Ash’s first tournament appearance was in the Indigo League, where he managed to make it to the Top 16. Here, he was pitted against his friend and rival Richie in a 3 on 3 battle. The battle was progressing well for Ash initially, but when Ash went down to his last Pokemon, Charizard, it refused to obey him, not wanting to fight what it was a weak opponent. Charizard took a nap on the field, and was subsequently disqualified, giving Richie the win.
To be fair to Ash, he was harassed by Team Rocket for quite a while before the battle, even arriving late to the stadium due to their antics. Ash’s other Pokemon were weakened, making Charizard his only hope. It was the first time that Ash had to face an opponent in a big tournament, but he could at least acknowledge how much he had learned, and how much further he had to go.
1
Ash’s Unova League loss was unbearable
Episode: Pokemon Black and White, “Cameron’s Secret Weapon!” and “A Unova League Evolution!”
Ash’s worst loss of all time was undoubtedly in the Vertres Conference of the European League, where he went up against Cameron. Cameron was an inexperienced trainer who didn’t understand basic concepts like type advantages, and really had no business being in the tournament to begin with. In his full battle with Ash in the quarter-final round, Cameron didn’t even bring a full team of 6 Pokemon, instead only having 5 in his command. Despite this disadvantage, Cameron manages to beat Ash handily, having his Riolu evolve into Lucario mid-battle.
This loss represented Ash’s only time performing worse than he had in a previous tournament, only making it to the top 8 instead of the top 4 as he did in Sinnoh. Ash reflects on his loss in the empty stadium afterward, vowing to continue striving for a tournament win—which he would one day achieve in Alola. Given his step down in performance and loss to an embarrassingly inexperienced trainer, there can be no doubt that Ash’s Unova League defeat was the most devastating loss he had ever suffered in the Pokemon Anime.