Although fans bash on Ash for never winning the Pokémon League, he has battledーand wonーagainst many strong Trainers. He has recently even won a Pokémon League, although the payoff for fans was 20 years of waiting. Throughout the Pokémon anime, Ash has either been destroyed or has beaten certain Trainersーwhether that be by a hair's breadth or a landslide.
Whether that be his rivals, friends, or allies he met along his journey to become a Pokémon Champion, Ash has faced many strong Trainers along the way. Here are the 7 strongest Pokémon Trainers Ash beat, ranked from impact, and how powerful they were in battle.
7 Stephan
Stephan was Ash's rival when he went to the Unova region and first made his debut in Pokémon the Series: Black & White. Although their first battle ended up being postponed, they once again battled for a second time, Stephan with his Blitzle and Ash with his Oshawott.
Even after Stephan decided to power up his Pokémon, he ultimately ended up losing to Ash, leaving him impressed with Ash's skills with Pokémon and as a fellow Pokémon Trainer.
6 Gladion
Gladion is a newer rival to the anime and one who appeared in Pokémon the Series: Sun & Moon. Despite his prickly attitude, he wasn't a bad person and very lenient for a rival compared to Ash's other ones. He even allows his Pokémon to battle each other and train by themselves, showing how kind of a person he is in the end.
His team of Pokémon were strong, causing Ash to lose to him a couple of times until he finally won against his Lycancroc with his own after they had a double knockout with Pikachu and Zoroark.
5 Blaine
Blaine is an odd character, as he is a Pokémon Trainer in Pokémon Masters EXーa free-to-start mobile gameーbut called a Gym Leader in the main entries of Pokémon games. Whatever the case, this means Blaine counts as both a Pokémon Trainer and a Gym Leader.
Ash battled against the Fire-type old man with Pikachu, making for one of the hardest battles he faced yet once he went up against Magmar. However, Ash once Charizard decided to go up against Magmar, it ultimately won him the gym badge in the end. Although fighting fire with fire doesn't make much progress in the games, Charizard allowed Ash to win against Blaine.
4 Gary Oak
Gary is the original rival for Pokémon fans of the original game as well as the anime. Although he was a jerk through and through, he was Ash's childhood friend and former rival who beat him countless times before becoming a Pokémon Researcher.
Not only did he have it in him to train his Pokémon, but he breezed through Pokémon Gyms and caught way more than Ash ever did in a short span. It wasn't until Ash used his Charizard against Gary's Pokémon that he finally won his first battle against Gary. This is also a feat that showed how strong Ash's Charizard was, despite the fact he never listened to him.
3 Noland
Noland was the Frontier Brain at the Battle Frontier's Battle Factory, but he still counts as a Pokémon Trainer as he was neither that nor a Gym Leader. He first made his debut in Pokémon the Series: Ruby and Sapphire. Ash wished to battle Noland's Articuno with his Charizard who still wouldn't listen to him to this point.
Ash ended up winning the battle with his Charizard despite Noland's strategic prowess as a Frontier Brain. This is an extremely impressive feat, considering Articuno is a Legendary Pokémon, and this would be near to impossible if it was the actual game.
2 Sawyer
Sawyer was quite the big deal when he first appeared as a rival for Ash in Pokémon the Series: XYーwith their climactic battle is one of the highlights of the entire anime. Although they have battled, trading between winning, losing, and even tieing, their battle in the episode "A Riveting Rivalry" was perhaps the most exciting.
After a double knockout against Sawyer's Slurpuff and Ah's Goodra, he then sent out Greninja as his final Pokémon. This highlight showed how powerful Greninja was as a whole, as without it, Ash would have lost the battle. After avoiding the move Frenzy Plant, Ash-Greninja used Water Shuriken and defeated his Mega Sceptile. Their battle would remain as one of the most hyped Pokémon battles in the entire anime.
1 Paul
Other than Gary, Paul is perhaps the other well-known rival who made his debut in Pokémon the Series: Diamond and Pearl. He first challenged Ash to a three-on-three battle, to which it resulted in a tie. Afterward, he defeated Ash countless times, not really giving Ash any credit for being a Pokémon Trainer and caring about strength over anything else.
This is why Ash decided to take his Chimchar, to which it evolved into Infernape under his care in comparison to his cold and condemning ways with it. Paul ultimately lost to Ash when they encountered each other again in the Lily of the Valley Conference, although it was not easy. After their battle, Paul also learned to respect Ash as a Pokémon Trainer.