Throughout Pokémon, Ash Ketchum has attained victories even when all the odds are against him. However, there are occasions when even his indomitable beliefs in his Pokémon cannot allow them to pull through.
While Ash is notorious for losing in the anime, it doesn't keep him from giving it his all and coming close. However, there are battles where Ash has failed, and his opponent managed to outplay him significantly and even have more than one teammate remaining. These battles rocked Ash and his Pokémon to their core and sometimes made him doubt himself as a Pokémon trainer.
10 Flint's Infernape Pummeled All Three Of Ash's Pokémon
Before his 8th gym battle, Ash squares off against Elite Four member Flint to reignite gym leader Vokner's passion for battling. Ash uses his Buizel, Infernape, and Pikachu, while Flint merely uses his Infernape, with no need for his other teammates.
Flint's Infernape quickly defeats Buizel and Ash's Infernape in one hit, without the latter two scoring a single blow. Pikachu lasts longer, but despite managing to deal damage with a few attacks, they do minuscule damage, and it repeatedly emerges as the worst of their clashes and eventually falls.
9 Anabel's Alakazam Proved To Be An Overwhelming Force
In an attempt to win the Ability Symbol as part of the Battle Frontier Arc, Ash had to face the Psychic type trainer, Anabel. Anabel used her Alakazam and Metagross against Ash's Corphish, Tauros, and Pikachu.
Alakazam's Psychic-type prowess allowed it to take out Corphish and Tauros without much of a fight. Pikachu manages to defeat it but not without Alakazam inflicting substantial damage that helped her Metagross to finish the job, handing Ash his first loss in the battle frontier, without him even facing a whole team.
8 Drake Took Down Ash's Confidence A Few Pegs
During his Hoenn travels, Elite Four member and sea captain Drake invites Ash aboard his ship for a best-of-three battle. Ash uses his Pikachu and Grovyle, while Drake utilizes his Shelgon and Altaria.
Although Ash is confident and launches aggressive blows, Drake consistently showcases his control over the battle through solid concentration. While Ash and Grovyle momentarily turn things around in the second fight, Drake's sudden choices during battle catch Ash off guard, lead him to lose both bouts, and ultimately rethink his battling style.
7 Trip Began A Tough Road For Ash In The Unova Region
In the first episode of the Black and White series, Ash arrives in Unova and meets a starting trainer named Trip. Shortly after Trip chooses a Snivy as his starter Pokémon from Professor Juniper's lab, he decides to test Pikachu's strength.
Pikachu cannot use its Electric attacks due to an encounter with the legendary Pokémon, Zekrom. Despite Ash having sufficient non-Electric type moves, Snivy defeats Pikachu with a combination of Tackle and Leaf Tornado. It's particularly baffling as Pikachu tied with a Latios three episodes earlier.
6 Ash's Battle With Paul's Honchkrow Devastated His Grotle
A while after winning his fourth Sinnoh gym badge, Ash winds up battling his rival Paul again in a one-on-one battle. Ash pits his Turtwig against Paul's Honchkrow.
Despite Turtwig having a type disadvantage, Turtwig manages to evade Honchkrow's super-effective attacks with its formidable speed. Unfortunately, the poor matchup catches up with Turtwig, and it suffers repeated blows. Turtwig evolves into Grotle but can no longer move as swiftly as it used to, leading Honchkrow to knock it out. Grotle recovers but is left crushed at its inability to run.
5 Ash's Second Battle With Trip Didn't Improve Things
Shortly after winning his first Unova gym badge, Ash once again meets his rival, Trip. Trip is initially reluctant to battle Ash, given their previous encounter and that Ash only has five Pokémon, but eventually agrees to a five-on-five battle.
Trip only uses three Pokémon, while his other two are left unknown. One of them almost instantaneously disposes of Ash's first two Pokémon. Ash's Pikachu and Snivy succeed in scoring a few victories, only to fall in their next round. In the end, Trip informs Ash that aside from Pikachu and Snivy, his other team members were poor. To make matters worse, none of these team members get justice in the future.
4 Ash Had No Chance Against Tobias From The Start
After Ash defeats Paul at the Sinnoh league, he gets paired in the semifinals against a trainer named Tobias. People knew little about Tobias except that he blazed through the gyms and the tournament with nothing but his Darkrai.
Sure enough, when Ash faces him, Darkrai wastes no time knocking out half of Ash's team members in one hit. Ash's Sceptile manages to hand Tobias' Darkrai its first defeat, but Tobias' Latios swiftly stops Ash's momentum. Pikachu tries to mount a comeback, but it ends in a tie that leaves Ash with no remaining Pokémon and Tobias with four.
3 Ash And Sawyer's Third Battle Proved That The Latter Was Not Someone To Underestimate
During Ash's travels with Kalos, he befriends a fellow trainer named Sawyer, who looks up to Ash. Despite his best efforts, Sawyer wound up losing their first two battles.
However, in their third battle, Sawyer shows off his growth. His Doublade doesn't go down without a fight. His Clawitzer takes out two of Ash's members, and he trains his Sceptile to memorize Ash's Greninja's battle style, which grants him the win. The victory proved that Sawyer was catching up to Ash. It made him a formidable foe in the Kalos league.
2 Ash Lost To Brandon Twice In A Row
As part of the final test of the Frontier saga, Ash had to face the Pyramid King Brandon. Ash gets possessed by an evil spirit during his first battle and ultimately loses despite having a type advantage.
However, during their rematch, Ash is in control. He again has a type advantage against Brandon's Registeel with his Torkoal. Despite Ash's unorthodox strategies, Brandon bests him again, making it one of the few times Ash has failed at a rematch. The loss forced him to gather his original team members to understand being at one with his Pokémon.
1 The Battle At Lake Acuity Made Ash Doubt His Career
From the moment Ash and Paul met, they stood their ground about believing their opposite approaches to training were the correct ones. Their first six-on-six battle on the shore of Lake Acuity put their beliefs on the line. Paul uses teammates based on his previous battles with Ash, while Ash uses the Pokémon he caught in the region.
Paul gains the upper hand throughout with his advanced strategies and meticulous substitutions. Although Ash's Chimchar evolves in response to his confidence, Ash loses, only knocking out two of Paul's Pokémon, giving him his worst defeat. As Paul leaves, Ash is left in tears with this loss.