Over the years, Ash Ketchum has won many battles. He has started out as an underdog and slowly built a match in his favor, and he has played against those who never stood a chance against him. He has courted controversy too—his loss against a certain character in the episode titled “Down to the Fiery Finish!” having left many fans annoyed. Through it all, though, he has learned from his mistakes and improved his tactics. And since he’s the protagonist of Pokémon, fans have gone on this journey with him.
Fans have shared the joy with him in his moments of exhilaration—having acquired a rare Pokémon or spending time with his friends—and fans have cried tears of frustration with him—when things have not gone his way, and he has lost a battle that was just within his reach.
10 Overconfidence Makes Him Lose Against Surge
In “Electric Shock Showdown”, Ash and his friends are in Vermilion City to meet the Gym Leader of that region, Lt. Surge, and have a possible battle with him. But there is a problem: Pikachu is injured and Ash is worried, even more so when the trio chance upon a slew of wounded Pokémon that were defeated by Lt. Surge’s Raichu (Pikachu’s evolved form).
Still, Ash is confident. And later, when they finally meet Lt. Surge and his Raichu, there is no dip in his conviction. No matter how hard Pikachu tries though, he is unable to use his electric powers to defeat Raichu, and ends up in a hospital bed instead. It’s a humiliating defeat, but Team Ash doesn’t give up, using Pikachu’s agility to win against Raichu in a later rematch.
9 A Mid-Battle Evolution Trips Ash
Ash is at the quarterfinals of the Unova League, up against Cameron, and is just as confident about winning the game as his adversary is. While Cameron sends in a fleet of Hydreigon, Ferrothorn, Samurott, and Swanna, Ash counters them all with a battalion of Boldore, Oshawott, Pignite, Pikachu, and Unfezant.
Either side could have won the match at this point if Cameron hadn't sent Riolu into the fray and the Pokèmon hadn't evolved into Lucario in the middle of the battle. There wasn't much Ash could do to recover from the incident, even though he tried to salvage the game by throwing an already lethargic Pikachu into the mix.
8 Charizard Almost Defeats Blaziken
At the Johto League, Ash is in the middle of a match with Harrison where they are both using Fire-type Pokémon. Ash has Charizard on his side, and Harrison has Blaziken with him.
Banking on their fiery power, both Charizard and Blaziken use Flamethrower on each other. Several dodges and hits follow, until it seems like Charizard has been able to defeat Blaziken. The referee thinks so too, and is just about to call the match in Ash’s favor, when Blaziken rises up from the ground and starts attacking Charizard again. Their fights go on for so long that, by the end, they are both very tired. And Charizard loses only because he is a lot more exhausted than Blaziken.
7 Darkrai And Latios Thrash Pikachu and Co.
Ash's match with Tobias, at the semi-finals of the Sinnoh League, doesn't start off on a good note. Three of his Pokèmon—Heracross, Gible, and Torkoal—are handed humiliating defeats by Tobias' Darkrai, but then Ash lets loose Sceptile on the Pokèmon and finally begins to lead the contest.
It's a momentary respite, though. For, soon, Tobias comes out with Latios and defeats two more from Ash's group. Even a late-match resurgence added by Pikachu isn't enough to turn the tide in Ash's favor.
6 Fletchling Comes Very Close To A Victory
Ash’s battle at Santalune Gym starts with Viola sending her Surskit against his Pikachu, who tries many attacks but is ultimately unsuccesful at defeating Surskit. Ash then, next, releases Fletchling into the field who dodges all the attacks and carefully uses Razor Wind to defeat Surskit.
Those on Ash’s side—Bonnie, Clemont and Serena—believe that he’ll be able to win the match easily now, but Viola cautions them and tells them to be patient, before unleashing Vivillon on Fletchling. And sure enough, one attack after another, hands victory to Vivillon.
5 Ash Is Handed An Icy Defeat
On his arrival, with his friends, at Snowbelle City, Ash goes about arranging a match with the Gym Leader of that region, a man called Wulfric. The field between them is an icy one, which causes problems the very second Ash releases Hawlucha and it loses its balance on the ice. Wulfric’s Pokémon, Abomasnow, seems to be a lot more comfortable with its surroundings, but then Hawlucha employs High Jump Kick and overpowers Abomasnow.
Next up, Wulfric sends Avalugg, who easily defeats Hawlucha. But then Ash comes out with Greninja—even transforming it to Ash-Greninja—and things get really tense for a while, until, ultimately, Ash-Greninja is overpowered.
4 Overexertion And Evolution Defeat Ash
In his battle with the surfing-obsessed Gym Leader Brawly, Ash chooses Taillow to start his attack against Brawly’s Machop. It doesn’t turn out to be a good idea, for Machop is too strong for Tailow. But then Ash releases Treecko who uses Pound And Quick Attack to finish off Machop.
As useful as Treecko is in the match, he is too tired to go on with it. Brock and Brawly notice it, and advise that he be let to rest, but Ash ignores them and in the end Treecko gets so exhausted that he has to be sent to the Pokémon Center to recover.
3 Pikachu Loses A Friendly Contest
In the episode titled “The Climb to Be the Very Best!,” Ash is fighting his Pikachu with Gigantamax Drednaw (in the absence of a Dynamax Band) when Leon comes across the three of them and gives him tactical advice on how a Drednaw can be defeated
Later, the two had a battle of their own, with Leon using it as an opportunity to teach Ash how Dynamaxing and G-Max Moves could be employed during a fight; he even gave Ash his own Dynamax Band. But, as much as Pikachu tried, and was victorious landing several attacks on Leon’s Charizard, it could not defeat the other Pokémon in the end.
2 Miltank Turns An Easy Match Into A Tough One
At Goldenrod City, Ash’s battle with Whitney starts as a face-off between Whitney’s Nidorina and Ash’s Cyndaquil. Nidorina employs many tactics, like Poison Sting and Tackle, but it doesn’t have an effect on Cyndaquil. Clefairy is sent to the field next by Whitney, but even that particular Pokémon is defeated by Cyndaquil’s Flamethrower.
Ash is quite confident at this point that it’ll be an easy win for him, but then the tables are turned when Whitney sends a Miltank and Ash’s battalion of Pokémon, including Pikachu, is unable to defeat it.
1 Ash Fails To Beat Alain At Kalos
The most controversial battle to date, Ash's match with Alain starts out favoring the former. It's the finals of the Kalos League, and both teams have powerful Pokémon on their side. Alain has Weavile, Unfezant, and others, and Ash has Pikachu, Talonflame, among a few more.
Even when Ash releases Greninja and Alain lets loose Charizard, it still looks like Ash will turn out to be the victor. But then there are transformations on both sides, with the two Pokémon turning themselves into Ash-Greninja and Mega Charizard X, respectively, and our hero suddenly finds himself losing the battle. While Ash was gracious in his defeat, fans on the other end of the screen weren't so happy with the decision. Many thought the outcome of the match to be extremely unfair.