Pokemon fans have been following Ash Ketchum through countless battles over the years. Many have seen his worst lows against intimidating rivals and strangers, as well as his several great achievements, like his victory over the Battle Frontier Brains and becoming the first Champion of Alola.
His track record has a fair number of wins and losses, but some of them are exceptionally bizarre. He’s won several battles that he had no right to win because of shenanigans or outside circumstances, and there are even some battles he’s lost that felt absolutely unfair given his clear and impressive skills as a trainer.
10 Should Have Won: Harrison (Silver Conference)
One of the dirtiest losses Ash has received was shortly after his Johto Gym Challenge, where he faced several opponents to reach the top levels of the Silver Conference. He had many great fights in this tournament arc, including a magnificent fight against Gary, but he also had a less graceful loss against a trainer from Hoenn named Harrison.
Ash’s losses usually have to do with him not being ready for the ludicrously powerful Pokemon that he has to prepare for, but Harrison’s team hardly featured anything overpowered. His biggest threats were the monumentally weak Kecleon and the weakness-heavy Blaziken, neither of which make for climactic losses.
9 Should Have Lost: Sabrina (Saffron Gym)
Fans of the early Pokemon series likely know how often Ash won badges without winning battles. Doing acts of service is a reasonable method of earning badges in the anime, but his win against Sabrina forfeiting at the sight of her long-lost friend Haunter is hardly worth this achievement.
The entire reason for this battle was that Ash lost and needed a Ghost-type to defeat her, and winning by not even using this new ally is hardly exceptional for Ash’s effort and preparation. It’s not too unusual for Ash at this stage of the anime, but it’s still one of his more underwhelming victories.
8 Should Have Won: Pryce (Mahogany Gym)
Sabrina isn’t the only Gym Leader who forfeited to Ash. During his Johto adventures, the battle for his seventh badge against Pryce led to an extremely difficult battle, with Ash’s Pikachu and Pryce’s Piloswine both taking tons of damage while Ash refused to give up at any opportunity.
Instead of persevering to victory, though, Pryce simply gives up when witnessing Ash’s ambition and courage. Ash even gets disappointed over this, thinking he didn’t win it properly while Pryce claims he was afraid of Piloswine being hurt, as if that isn’t just a normal part of nearly any Pokemon battle.
7 Should Have Lost: Conway (Lily Of The Valley Conference)
One of the things that makes the Pokemon anime great is the unique battle strategies that Ash and others use. In some ways, this can be quite impressive, and they can be refreshingly different from the turn-based combat of the games, but it also leads to some utterly ludicrous victories that hardly feel fair.
One of the most shenanigan-heavy matches has to be against Dawn’s pursuer Conway in Ash’s final Sinnoh tournament. While Conway used several unique strategies normally unique to the games like Trick Room to change the speed of his Pokemon, and stat-raising moves with his defensive Shuckle, Ash’s victories entirely rely on an unrealistically strong Gible using Draco Meteor directly in his opponents’ faces.
6 Should Have Won: Brawly (Dewford Gym)
One of Ash’s earliest losses in Hoenn was against Brawly, the Fighting-type Gym Leader of Dewford who’s an equally difficult opponent in the games. Even though Ash is an undoubtedly strong trainer, much of his loss was because of his ambition to battle after Brawly repeatedly delayed their fight to go surfing.
Brawly hardly comes across like a tough opponent in the anime, and the result of Ash’s loss is that he explores Dewford Town for several episodes before having a rematch. Not only does the loss itself feel unrelated to Ash’s skill at this time, but his later win using a Corphish he catches is hardly a sign that the extra training was worth it.
5 Should Have Lost: Trip (Vertress Conference)
Among all of Ash’s rivals, Trip is easily one of the most forgettable of the entire series. This Unova rival is essentially like a boring version of Gary, obsessed with becoming a powerful battler with little regard for his Pokemon and a condescending attitude towards Ash and his friends.
This boring rivalry ends with an even duller battle in the Ventress Conference, consisting of a simple one-on-one match between Ash’s Pikachu and Trip’s Serperior. This would’ve been a great opportunity for a tournament loss to humble Ash, or been a more dramatic battle with more of his team, but instead, this feels like a cheap and easy win to wrap up this lame rivalry.
4 Should Have Won: Whitney (Goldenrod Gym)
Whitney is infamous in Pokemon Gold & Silver for an oddly-challenging Miltank. Lacking many weaknesses and having such high defensive stats makes her oddly difficult in this stage of the game, but Ash’s ability to use unusual gimmicks and strategies can easily give him a great edge.
Instead, Miltank simply does what it does in the game and annihilates Ash’s Pokemon after Ash takes down the rest of her team fairly easily. Whitney can catch many new trainers off-guard, but Ash is far too experienced to have lost this stereotypically.
3 Should Have Lost: Misty (Cinnabar Island)
Many fans know Togepi as Misty’s handheld companion, but few people remember the exact day it hatched. Ash, Misty, Brock, and even Team Rocket all wanted to have Togepi for themselves when it cracked open on Cinnabar Island, and even had a small tournament that Ash managed to win.
Even though he should’ve owned the new Pokemon, though, it simply walks over to Misty and wishes to be with her. This would’ve been a great way to show how Misty is still a strong fighter and make her ownership of Togepi feel more earned, but instead it’s based more around Togepi’s newborn intuition and makes for an unnecessary win on Ash’s record.
2 Should Have Won: Drew (Fallarbor Town)
Ash is hardly the only one to have rivals. During his Hoenn adventures, his companion May was always at odds with Drew during the course of her Contest Challenge, a graceful trainer with powerful techniques unlike any other trainer. Since Contests are a different skill than straightforward battles, it seems that Ash should have an edge over these sorts of specialized trainers.
Instead, May’s main rival Drew manages to beat Ash in a battle quite early in the series. This win makes Ash’s disinterest in contests feel pointless, as it’s clear that battle skill is much more related to contests than the anime makes it seem, and it would’ve made far more sense for Ash to win in his area of skill.
1 Should Have Lost: Tate & Liza (Mossdeep Gym)
One of the biggest things introduced in the Hoenn games and anime were Double Battles, a new form of tag team fights that could let more Pokemon fight and new strategies prosper. This made great waves in competitive Pokemon circles, but this was also great for the anime as an introduction to many new challenges for Ash to take on.
However, one of his first major double battles against the twin Gym Leaders Tate & Liza makes it clear that Ash doesn’t need to learn new skills to succeed. He beats both of them quite easily, even though the two of them fight him after they’ve freshly rejuvenated their strained sibling relationship. The odds were absolutely in Tate & Liza’s favors, making Ash’s win feel unearned.
