Summary

• Ash Ketchum, after 25 years, finally became a regional League Champion at the Manalo Conference, making him the first Champion in the Alola region's history.
• Ash's loss at the Lily of the Valley Conference still stings, as he displayed remarkable maturity and strategy, only to be defeated by Tobias's powerful Pokémon.
• Ash's victory at the Masters Eight Tournament, where he defeated the undefeated Champion Leon, fulfilled his dream of being the best Trainer and saw him crowned the Monarch of the World Coronation Series.

Ash Ketchum was on his Pokémon journey for twenty-five years. He's been to eight different regions, befriending and catching all kinds of Pokémon on his way to become a Pokémon Master. Competitive and relentless, Ash has also participated in numerous championships, often placing among the Top 10 and nearly reaching victory twice. It took seven tries before he became a regional League Champion, though.

Below is every tournament and championship battle that Ash has ever had, including the ranking at which he finished. The entries are listed in chronological order, starting with Ash's first conference performance. Ash has also participated in many smaller tournaments, but those aren't considered here; instead, only the regional Leagues' big conference tournaments are counted.

1 Indigo Conference - Top 16

Series: Pokémon (The Original Series)

The Indigo Conference is the first championship Ash participates in, explaining why it's also his lowest placing in a Pokémon League so far. Still, Ash makes it to the Top 16 out of 200+ contestants, which is no easy feat.

Ash loses against Richie, who fans as the Trainer who seemed like an Ash clone, to the point where he also had a Pikachu. The battle is exciting enough, but Ash loses because his Charizard refuses to obey his commands. Instead, it lies down and takes a nap, leading to Ash's disqualification. Ash was still an inexperienced Trainer back then, so it makes sense that he lost this tournament. He simply wasn't ready to go all the way.

2 Orange League - Champion

Series: Pokémon: Adventures in the Orange Islands

Ash first became a Champion during the Orange Islands arc in the original saga. His final battle is against Drake, the notorious Dragon Master. The match ranks as one of the anime's most exciting, as Drake's Dragonite single-handedly defeats four of Ash's Pokémon before being taken down by Pikachu.

The Orange Islands were created for the anime, and the storyline took place early in the series, so many casual fans don't know about Ash's victory at the Orange League. It wasn't a tournament-style like the other anime Leagues, but was more like the games, with Ash battling against the region's champion directly. Still, besting Drake in battle was one of Ash's best moments as a Trainer, and cemented Pikachu's spot as his secret ace.

Pokémon: Adventures in the Orange Islands is the Second Season of the original show, and it's available to stream on Prime Video.

3 Silver Conference - Top 8

Series: Pokémon: Master Quest

Harrison was one of Ash's best rivals in Pokémon, acting as both a wise mentor and challenging opponent who pushed him to become a better Trainer. The Silver Conference also made Ash more cunning, and even though Harrison bested him in battle, their match was one of the series' most thrilling.

The Silver Conference also sees Ash facing Gary in one of the Pokémon anime's most unforgettable and rule-breaking battles. He comes out on top, and his rivalry with Gary officially comes to an end. After his loss to Harrison, Ash ends up placing in the top 8, but fans could see the young Trainer was already on his way to greatness.

Pokémon: Master Quest is the Fifth Season of the original show, and it's available to stream on Prime Video.

4 Ever Grande Conference - Top 8

Series: Pokémon: Advanced Battle

In Hoenn, Ash entered the Ever Grande Conference and once again placed in the Top 8. This time, he loses against the conference's eventual winner, Tyson, in a truly bizarre battle. Going into the march's second half, Tyson and Ash seemed evenly matched. Ash's Torkoal bested Tyson's Shiftry, but the latter's Hariyama defeated two of Ash's Pokémon, Torkoal and Corphish. In the end, it all comes down to a battle between Ash's Pikachu and Tyson's Meowth. Both Pokémon put up a valiant effort, but Meowth came out on top after a particularly energetic Iron Tail caused Pikachu to collapse.

Pokémon: Advanced Battle is the Eighth Season of the original show, and it's available to stream on Prime Video.

5 Battle Frontier - Champion

Series: Pokémon: Battle Frontier

Following Ash's time in the Ever Grande Conference, Ash ran into a man named Scott and was invited to compete in the Battle Frontier, a special competition where Trainers would travel around Kanto to compete against the seven Frontier Brains and their various challenges. Much like the Orange Island Conference, the competition didn't pit Ash against any other Trainers, and the challenge was simply to see if he could overcome the Frontier Brains.

Ash eventually defeated all seven Frontier Brains, meaning that the Battle Frontier was the second major competition Ash won in the anime. Ash was then given the chance to become a Frontier Brain, himself, and while he declined the offer, Scott said that he could take him up on it at any time.

Pokémon: Battle Frontier is the Ninth Season of the original show.

Ash clearing the Battle Frontier became even more impressive in Diamon and Pearl where it was revealed that Paul's older brother Reggie never defeated the strongest Frontier Brain, Brandon; that, coupled with Paul's loss to Brandon, retroactively made Ash's victory and overall skill all the more impressive.

6 Lily Of The Valley Conference - Top 4

Series: Pokémon Diamond & Pearl: Sinnoh League Victors

Ash's loss at the Lily of the Valley Conference still stings During his journey across Sinnoh, Ash exhibited real maturity and growth, making many in the community believe he would finally become the Champion. His battle against his reformed rival, Paul, seemed to confirm this, as Ash showed remarkable strategy and composure that eventually led to his victory.

Alas, things didn't go according to plan. Ash faces Tobias in the semi-finals, and he is no match. Tobias has a Darkrai, a mythical Pokémon. Still, Ash manages to defeat the Pokémon with his Sceptile. Tobias doesn't even sweat because his next Pokémon is Latios, a Legendary, and although Pikachu ends up fainting, it takes Latios down with it. However, Ash no longer has any Pokémon left, and Tobias wins the match. Many fans still consider it unfair that Tobias won by using a Mythical and a Legendary, and they might have a point.

Pokémon Diamond & Pearl: Sinnoh League Victors is the Thirteenth Season of the original show.

7 Vertress Conference - Top 8

Series: Pokémon Black & White: Adventures in Unova and Beyond

During Unova's Vertress Conference, Ash's Pikachu once again takes center stage, acting as its Trainer's last hope. In his battle against Cameron, Ash chooses a balanced team of 6, but Pikachu is the only one left standing when Cameron takes out his newly evolved Lucario. The electric mouse performs irably but succumbs to the mighty Lucario, one of Generation IV's best mons. Ash takes his defeat with maturity and places among the Top 8 again, actually going down in rankings for the first time ever.

Pokémon Black & White: Adventures in Unova and Beyond is the Sixteenth Season of the original show.

8 Lumiose Conference - Runner-Up

Series: Pokémon XYZ

If Ash's loss at the Lily of the Valley Conference stings, then his loss against Alain at the Lumiose Conference outright burns. Ash makes it to the finals with one of his best teams in the series: Pikachu, Greninja, Noivern, Talonflame, Hawlucha, and Goodra. Alain's team is no joke either, and his Charizard is a menacing foe similar to Tobias' Darkrai.

After a gruesome battle, both Trainers are down to their last Pokémon, Ash-Greninja and Mega Charizard X. Both Pokémon fire their attacks at once, creating a massive cloud of steam. Once the fog clears and after an intense stare-off, Greninja succumbs, leaving Ash as the runner-up. Alain's victory at the Lumiose Conference is still controversial among the community, as many feel that Ash was at the top of his game during the Kalos season.

Pokémon XYZ is the Nineteenth Season of the original show.

9 Manalo Conference - Champion

Series: Pokémon Sun & Moon: Ultra Legends

The news went around the world: after twenty-one years, Ash Ketchum finally won a canon Pokémon League. As previously mentioned, it wasn't entirely true because Ash was already the Orange League Champion. Still, his victory at the Manalo Conference made him a regional Champion, an honor that only the best trainers achieve. Furthermore, he was the region's first Champion ever, making the whole thing even more noteworthy.

Ash's last opponent is Gladion, one of Sun & Moon's best characters. It all ends when Ash's Lycanroc uses Counter, sending Gladion's Lycanroc out of the field and winning Ash the match. It was a triumphant moment for every fan, a victory twenty-one years in the making, and one of the anime's most satisfying moments to date.

Pokémon Sun & Moon: Ultra Legends is the Twenty-second Season of the original show.

10 Masters Eight Tournament - Monarch

Series: Pokémon Ultimate Journeys

Ash didn't compete in the Galar League and earn badges there; instead, Ash used his win in Alola to enter the World Coronation Series, a tournament designed to find out who's the best of the best, with competitors like Gym Leaders and regional Champions in the mix. Ash earned his way into the World Coronation Series' final tournament, the Masters' Eight, which featured some of Pokémon's most skilled trainers.

Ash fought hard in the Masters Eight, going up against Steven Stone, Cynthia, and finally the undefeated Leon, Champion of Galar. Ash's match with Leon was incredible, featuring Mega Evolution, Z-Moves, and Dynamaxing, and it was a hard-fought battle on both sides. Ash and Leon's match eventually came down to Pikachu versus Charizard, with Pikachu drawing strength from every Pokémon Ash ever caught in order to win. Ash was crowned Monarch of the World Coronation Series, the title given to the strongest Pokémon Trainer, effectively achieving his dream of being the best that no one ever was.

Ash's victory against Leon finally made him the world's greatest Pokémon Trainer, and it was very much earned. It was one thing that Ash had one of his strongest teams to date, but by Ultimate Journeys, Ash's experiences as a Pokémon Trainer across so many leagues and competitions made him more skilled than he had ever been before, so there was no room for any of the mistakes he made in his previous losses. Ash had everything going for him in the Masters Eight, so it makes sense that he won there when his past endeavors usually ended in failure.

In addition to Ash's increased battle prowess, the team of Pokémon he used was filled with heavy hitters. Aside from Pikachu, every Pokémon was full evolved, meaning that team like Dragonite, Gengar, and Lucario could fight at maximum efficiency. Those three Pokémon in particular are some of Ash's strongest ever. All of this combined with Ash's increased battling skill meant that Ash truly had never been in a better position to win a tournament.

Though his Pokémon journey may be over, a producer for the anime has hinted that Ash may return to the Pokémon anime.

On a meta-level, it also made it the best way to end Ash's story. Not long after Ash defeated Leon, it was announced that the anime would receive a soft reboot in Pokémon Horizons, so it was probably decided that Ash needed to go out on as big a win as possible so his story could end on a high note. That line of reasoning worked out very well, of course, as Ash becoming the world champion was the most satisfying way to end both his character arc and the original Pokémon anime, and that's unlikely to ever be topped.

Pokémon Ultimate Journeys is the Twenty-fifth Season of the original show.