Since debuting in 1998, the Pokémon anime has chronicled the adventures of Ash Ketchum and his friends. Ash's goal from day one has been to become a Pokémon master, which involves him challenging the various leagues to defeat their champions. Though he's won a few leagues here and there, his biggest achievement has been his victory over Leon, champion of the Galar region.

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The road to this Ash's journey to becoming a Pokémon master has been extended, arduous, and hampered by many battles. Due to the anime's often questionable writing choices, some of these victories for Ash and his friends feel lackluster or unearned.

Ash vs Richie

Ash and Richie realize they will be facing one another in the Indigo League

After achieving the eight gym badges in Kanto, Ash was ready to take on his first-ever Pokémon league. He started off well thanks to making use of some surprising Pokémon he acquired in his journey and even managed to outlast his rival, Gary Oak. Things take a turn for the worse when he has to face Richie, a fellow novice trainer whose team eerily mirrors Ash's.

First off, Ash is hounded by his long-time nemesis, Team Rocket, meaning that his Pokémon aren't in fighting shape when he arrives to face Richie. While Ash does beat Richie down to his last Pokémon, a Pikachu, he ultimately loses in a heartbreaking moment in the series due to his Charizard refusing to obey him, and the judge deciding that Squirtle couldn't battle after being put to sleep. It's understandable if Ash lost his first try at a league, but the writers could have come up with a fairer circumstance.

May vs Solidad

Solidad is here to crush May's dreams of winning the Ribbon Cup

As the first female companion to replace fan-favorite, Misty, May had an uphill battle in winning over fans. Fortunately, she succeeded thanks to her student-trainer relationship with Ash, her development from fearing Pokémon to loving them, and pursuing a career in Pokémon contests. Like Ash, May had her own rivals to overcome, and slowly and steadily improved her craft.

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Which made it all the more heartbreaking and annoying when she faced Solidad. Introduced as the woman who defeated May's long-time rival, Drew, Solidad went against May in the final round for the Ribbon Cup and defeated her by a landslide. Worse, this came moments after May's long built-up showdown with Drew, making the moment feel like a rushed cliff note in an otherwise solid arc.

Ash vs Tate and Liza

Pikachu and Swellow powered up with Thunder Armor

During his journey through the Hoenn region, Ash had to face off against Tate and Liza. These twin gym-leaders specialized in Psychic-type Pokémon and fight their opponents in double battles. For his match, Ash chose Pikachu and his speedy Swellow to take down their duo of psychic Rock-types, Lunaton and Solroc.

What makes this gym battle stand out as one of the most frustrating in the anime is how Ash wins. By having Pikachu fire one of its thunderbolts upon itself and Swellow, it coats them in lightning armor. It's no secret that the Pokémon anime has always played fast and loose with rules, but nothing about this strategy makes sense, especially since it is never used again.

Ash vs Trip: Round One

Trip taking a photo of Ash's Pikachu before his Snivy does battle with it.

As with the previous two regions, upon arriving in Unova, Ash ran into a new trainer who had just picked his first Pokémon from the regional professor. The boy, Trip, would not become one of his companions, as he had nothing but contempt for the Kanto region. He decided to test his new Snivy against Ash's Pikachu, beginning their rivalry.

To everyone's surprise, this Snivy that had never battled before defeated Ash's Pikachu, who at this point was a veteran of five leagues and recently tied against a Latios. The reason given was that an encounter with the legendary dragon, Zekrom, had left Pikachu without access to Electric-type moves. Fans were quick to call this out as the weak excuse that it was to justify Trip as Ash's new rival and to have him go back to basics for this arc.

Ash vs Tobias

Ash's Sceptile defeats Tobias' Darkrai

The Sinnoh league saw some of Ash's best character growth in the series up to that point. From rocky beginnings, Ash put together a strong team and overcame Paul, perhaps his greatest rival to date. Unfortunately, the writers weren't yet ready to let Ash win a Pokémon League, and wanted to once again hammer in that there will be those who are better than you.

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Enter Tobias, an unknown trainer who gained attention at the League for using the mythical Pokémon, Darkrai, who can put opponents to sleep with its Dark Void attack. Ash was able to defeat it at the cost of half his team, but Tobias immediately followed up with a legendary Dragon-type, Latios. This fight is enraging to watch because of its hopelessness, as no matter how much Ash trains, the writers could create whatever they wanted to stop him.

Ash vs Elesa

Ash getting yelled at by his Pikachu

Ash has been no stranger to unconventional methods of obtaining a gym badge. Most of these came during his Kanto days, when he was new and didn't have the same experience he has now. Unfortunately, during the Unova era, the writers made Ash regress to his Kanto days, resulting in slip-ups like his battle with Elesa.

At first, Ash's strategy seems sound: use his newly caught Ground-type, Palpitoed, against Elesa's Electric-types. When Palpitoed is knocked out, however, Ash didn't bring any backup Pokémon, so has to run from the gym to get more mid-battle. He manages a win, but he really should have been disqualified.

Dawn vs Iris

Dawn's Mamoswine facing off against Iris' Dragonite

During his travels, Ash picks up a number of traveling companions, most of whom are prominent characters from the Pokémon games. One of the strongest in both character and talent is Dawn, a young girl from Sinnoh with dreams of winning Pokémon Contests. One of his weakest is Iris, an annoying girl with plans to become a Dragon-type master.

During the Unova Junior Cup, Dawn and Iris clashed with their strongest Pokémon: Dawn's Mamoswine whom she had bonded with from a Swinub, and Iris' newly caught Dragonite. Despite Dragonite disobeying Iris, and having a crippling weakness to Ice-types, it came out victorious. While it is understandable that the anime wants to focus on Ash's new companion, it's frustrating that it came at the cost of early lessons against using disobeying Pokémon.

Ash vs Cameron

Ash's Pignite landing an attack on Cameron's Hydreigon

Near the end of Ash's Unova journey, he ran into a young trainer with a Riolu named Cameron. This guy is easily among the most unskilled trainers in the anime: he knows nothing about type matchups, didn't know that you needed eight badges to enter the league, and brought five Pokémon instead of six to his match against Ash. And yet somehow he wins, because this was a time when Ash was not allowed to win a Pokémon league.

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This is easily one of the most frustrating battles in the entire series. Along with Cameron's incompetence and poor management of his Pokémon, Ash performs even worse than in his fight with Richie, when he was a novice trainer. The only good part is at the beginning, where Cameron gets a good lead thanks to using the rare and hard-to-evolve Dragon-type, Hydreigon.

Ash vs Alain

Ash's Ash-Greninja fighting Alain's Mega Charizard X

Ash's journeys through Kalos were seen by many as the highlight of his career. The team he put together was his strongest until Galar, and he unlocked a special transformation for his Greninja, allowing it to go toe to toe with Pokémon who can Mega Evolve. Yet when it came to the Kalos league, Ash came in second place behind a Mega Evolution specialist named Alain.

In all fairness, the fight was well-paced and animated, particularly when Ash's Greninja faced Alain's Mega Charizard X. However, the ending is abrupt and frustrating, which is due to a last-minute decision to have Ash lose instead of win. Once again, it felt like the anime was saying that, even when Ash is at his absolute best, he will never be good enough.

Ash vs Hau

Ash, Hau, Rowlet, and Decidueye shake after their match

Despite being the rival character in Pokémon Sun and Moon, Hau didn't appear in the anime until a few episodes before the Alola league. Despite this lack of screen time, his Decidueye developed a friendly rivalry with Ash's Rowlet, hinting at a future showdown. This would come during the league, though Ash's victory left many people baffled.

Despite taking place close to the end of the Alola arc, the battle retains its comedic tone, which places emphasis on gags. These include Rowlet somehow dodging a powerful Z-Move from Decidueye, and Rowlet falling asleep during the middle of the fight. This last point is especially egregious, since in the past Ash and friends had Pokémon disqualified for falling or being put to sleep.

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