Ash Ketchum's journey to becoming a Pokémon Master is a long and arduous one. Sure, he grows and improves as time progresses, but he's notorious for making unforgivable mistakes as a Pokémon trainer, resulting in many losses. Ash even loses to wild Pokémon on occasion.

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His initial adventures around Kanto see him lose pretty often, as he gets properly accustomed to his partner Pokémon and slowly gains their trust and loyalty. These losses often lead to him learning from them and winning a rematch, but they're still losses all the same.

10 Brock Humiliated Ash In His First Gym Challenge

Brock Vs Ash in Pokemon

Ash's first true test comes at the ominous setting of the Pewter City Gym, where he faces Rock-type specialist Brock. Although Ash eventually emerges with the badge, it's often overlooked that he never actually beat Brock. In fact, he loses their initial bout when Onix binds Pikachu and forces Ash to surrender.

After training with Pikachu in supercharging its power, he battles Brock once more, losing Pidgeotto to Geodude due to its obvious type disadvantage and setting the stage for the Onix versus Pikachu rematch. Onix is about to defeat Pikachu once again when the sprinklers turn on, weakening Onix enough to be defeated, but Ash can't bring himself to fight an opponent at such a disadvantage and forfeits.

9 Ash Was Merely A Stepping Stone Towards 100 Wins For A.J.

Ash, Pikachu, and AJ in Pokémon.

After picking up the Cascade Badge from the Cerulean City Gym, Ash challenges an undefeated trainer called A.J. who's won 98 battles. Although his Sandshrew doesn't seem too intimidating at first, it quickly knocks out Ash's Pidgeotto, pins down the helpless Butterfree, and after Pikachu refuses to become victim number three, A.J. counts the bout as his 99th victory.

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At this stage in his journey, Ash was still in his naïve and overconfident phase, and he's an especially sore loser after his match with A.J. His immediate thought was that because A.J. trained his Pokémon hard, that meant he didn't care for them at all, but he learned that wasn't necessarily the case.

8 Lt. Surge's Raichu Was Way Too Strong For Pikachu To Handle

Pokemon Electric Shock Showdown Raichu Pikachu Lt Surge Ash

Arriving in Vermillion City for his third Gym badge, Ash battles Electric-type specialist Lt. Surge. Pikachu is fired up for one of the first times in the anime and keen to battle Surge's Raichu. However, it is utterly dominated by Raichu's sheer power and strength, and due to Raichu having better Electric-type moves, Pikachu gets annihilated.

Ash wins the rematch when he calls upon a strategy to take advantage of Raichu's weakness of being slow, leading to the victory for Ash and him earning the Thunder Badge. Learning from defeat is a theme for Ash Ketchum, but this could arguably be avoided if he researched Gym Leaders before he challenged them.

7 Sabrina's Abra Evolved Mid-Battle And Easily Defeated Pikachu

pokemon-sabrina

Ash's battle with the Saffron City Gym Leader Sabrina is another case of Ash losing the initial battle but eventually emerging with the badge, without necessarily winning it outright. Ash rushes through the battle, thinking that Abra is an easy opponent. Sabrina's Abra uses Teleport to avoid Pikachu's attack before evolving into Kadabra.

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Kadabra's telekinetic powers help it turn the tide of the battle and knock out Pikachu with relative ease, forcing Ash to forfeit the match and subjecting Ash and friends to being shrunk down to doll-size as punishment for the defeat.

6 Anthony's Hitmonchan Was Too Much For Pikachu

Anthony and his Hitmonchan from the Pokémon episode The Punchy Pokémon

Ash and friends come across a Hitmonchan in the wild, and Ash thinks that he can teach Pikachu to beat Hitmonchan at its own game with punches, which naturally do no real damage. It's then that a trainer called Anthony emerges, who happens to be Hitmonchan's trainer. Anthony acts like a boxing coach and encourages Hitmonchan to attack, with it obliging and knocking Pikachu out easily for the victory.

While not set in a particularly conventional format, this was a battle and Pikachu was left unable to continue, meaning that it counts as a defeat for Ash.

5 Ash Called Duplica's Ditto Boring And Instantly Regretted It

ditto duplica pokemon anime

When caught in a torrential downpour of rain in "Ditto's Mysterious Mansion," Ash and friends take cover in a seemingly abandoned mansion. There they run into Duplica and her Ditto, imitating Ash and Pikachu. After hearing Ash and friends mock Ditto and its capabilities, Duplica challenges Ash to a battle.

Duplica's Ditto faces Ash's Bulbasaur, turning into Bulbasaur, as is tradition with Ditto. Ditto restrains Ash's Bulbasaur and forces him to forfeit, due to him caring about the well-being of his struggling Pokémon.

4 Ash Lost To Help Paras Finally Evolve

Pokemon Parasect

In "The Problem with Paras," Ash, Brock, and Misty meet Cassandra, who's trying to get her Paras to evolve into a Parasect, with the only catch being that it's too weak and cowardly to win any battles. Ash unsuccessfully attempts to throw some battles to give it wins but overdoes it and Charmeleon causes it to flee.

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After some coaching from Meowth and Team Rocket, Paras returns to battle Pikachu with Pikachu throwing the match, technically giving Paras a victory. Paras also manages to knock out Charmeleon when it goes out of control, causing it to finally evolve into Parasect. It may not have been a legit battle, but it was a victory for Paras all the same.

3 Keith's Farfetch'd Caught Bulbasaur By Surprise And Defeated It, But Lost To Misty's Psyduck

Farfetch'd Pokemon

In "So Near, Yet So Farfetch'd," a trainer called Keith and his Farfetch'd go around stealing everybody's Pokémon because Keith doesn't believe his Farfetch'd is strong enough to catch Pokémon through legitimate means.

When they eventually corner the thieves, Ash challenges them to a battle, but Farfetch'd turns out to be a tricky opponent, using Agility to turn the tide of the battle and ultimately knocking out Ash's Bulbasaur. Before Ash can call out another Pokémon, Misty steps in and has Psyduck defeat Farfetch'd, meaning that Ash's only contribution to this battle was watching his Pokémon lose.

2 Ash Lost To A Pokémon League Instructor When Using A Meowth, Weezing, And An Arbok

Pikachu Exam Board Pokemon League

Ash and friends visit the Pokémon League Admission Center so Ash can take an exam for a badge that will allow him to battle in the Pokémon League. After some theory-based examination stages, the final stage requires trainers to battle using mystery Pokémon to test a their ability to adapt to unforeseen situations.

Ash faces the instructor in a best-of-3 battle. Ash defeats Flareon with Weezing but loses his Arbok when he has it use Wrap on a spiky Jolteon. Finally, his Meowth gets instantly frozen by a Vaporeon's Ice Beam, losing the match for Ash.

1 Blaine's Magmar Was Too Hot For Ash To Handle

Blaine And Ash In Pokemon

After eventually solving a mystery stranger's string of riddles, Ash and friends find themselves at the Cinnabar Gym where the stranger turns out to be Gym Leader Blaine himself. Ash faces Blaine and his Ninetales, Rhydon, and Magmar, losing Squirtle to Ninetales, beating Rhydon with Pikachu, but after Charizard refuses to battle, Pikachu is left to face Magmar.

Facing the risk of a fearsome Fire Blast into a volcano, Ash chooses to save Pikachu and forfeits the match. Naturally, they end up having a rematch with Ash eventually earning the badge, but only because Charizard decides to fight on the second occasion.

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