Richie

Ash meets Richie in the lift in the Pokémon League. The lift breaks down, but Richie starts it up again with Pikachu's help. Later they meet again, when Team Rocket tricks everyone joining the League into giving them their Pokémon. Ash and Richie bust Team Rocket's plan, but later they find out that they have to fight each other in the fifth round of the League.

Ash nearly arrives late to the match beacause Team Rocket was after him, but Richie begs for more time and in the end Ash does arrive. Happy (Richie's Butterfree) beats Squirtle by putting him to sleep, and is then defeated by Ash's Pikachu. Zippo (Richie's Charmander) beats Pikachu with Flamethrower and Tackle, but is no match for Ash's Charizard. Then Richie sends out Sparky and Charizard knocks him over by stamping on the ground, but then Charizard decides it isn't worth fighting a little Pikachu and goes to sleep. Richie wins, but he and Ash remain friends.

In the next round Richie loses to Assumpta, whose Ivysaur defeats Sparky without any trouble. Later Ash and Richie promise each other to try hard to become Pokémon Masters. Richie leaves and he hasn't appeared in the series again yet.

In the comic Ash meets Richie after his first match. Ash is sitting at the Indigo League restaurant, and then wonders where Pikachu has gone. He sees Pikachu sitting with another Pikachu, that is eating some kind of food. Ash tells Pikachu not to bother strangers, but then Richie says that Pikachu isn't bothering anyone, and that his Chuchino likes eating with friends. Then he asks Ash if he was the Guy who made his Krabby evolve in the middle of the match and he asks how he timed it so well. Ash says it's a trade secret (like in the series it was a coincidence), and is embarrased because Richie watched his match, but he missed Richie's. Ash is just about to make something up about Richie's match when Richie realises that it is nearly time for his first match.

Richie wins the fight with only Chuchino. Ash and Richie become best friends, and they both win their second and third round. Richie tells Ash that he's amazing, because he gets more relaxed with every battle. Richie says he justs gets more nervous every time. Then he tells Ash he'd really like to meet him in the ring, and Ash says he'd like it, too.

The winners of the fourth round battle each other in the fifth round. In the fourth round Richie has to fight Gary (the battle isn't shown), and Richie wins. Ash also wins his battle, and he and Richie have to face each other in the next round.

Like in the series Richie uses Happy in the first round, and Ash uses Squirtle. Happy uses Sleep Powder, and Squirtle uses Skull Bash at the same time. Happy is knocked out by Squirtle, but Squirtle goes to sleep at the same time, so it's a draw. Then Pikachu and Chuchino fight each other in the next round, and they both fry each other with Thunder at the same time. Ash and Richie call for time out, and Richie says to Ash that this is their last chance, and that they should both use their secret weapons. Ash agrees and sends out his Charizard, and is shocked when he sees that richie also has a Charizard, Charley. But for some reason the Charizard start to fight on instinct, and Charizard ends up almost killing Charley. Richie tries to return his Pokémon, but it won't work. Ash recalls Charizard and leaves the ring, making Richie the winner, as his Charizard was still capable of fighting.

Ash tells Richie to win the sixth round for him, and then goes to cheer Richie on with Brock and Misty.