Ritchie first appeared in A Friend In Deed and quickly befriended his fellow Pokémon League competitor, Ash Ketchum, in an elevator. When the power in the elevator went out, Ritchie asks Ash if he can use Pikachu for his Thunder Shock attack to get the elevator running again, to which he agrees to and Ritchie opens the elevator's control box and has Pikachu use Thunder Shock on it, this causes the elevator to start working again. Later on, during Team Rocket's scheme to steal some Pokémon lead Ash and Ritchie to realize who they were and went after them, but they were unable to catch up to them so they camped out until the next day. Ritchie and Ash saw tire tracks and led them to Team Rocket's van. When they went inside, they were spotted by Team Rocket and the trio trapped them inside. Ash and Ritchie were able to escape with the Poké Balls retrieved from Team Rocket.
In the next episode Friend or Foe Alike, Ritchie and Ash battled in the fifth round at the Indigo Stadium and Ritchie was given the win when Ash's Charizard refuses to battle.
Later on in the episode Friends to the End, Ritchie loses the sixth round match. Ash later joins Ritchie near a lake. While their Pikachu play, both Ash and Ritchie talk about their losses. Ritchie says that he would have trained harder if he had known how tough the competition would be. He also comments on how losing is good for Trainers, and Ash and Ritchie then promise to become Pokémon Masters no matter what.
- Pikachu (nicknamed Sparky).
- Charmander → Charmeleon (nicknamed Zippo).
- Butterfree (nicknamed Happy).
- Pupitar (nicknamed Cruise).
- Taillow (nicknamed Rose).
- To differentiate his Pokémon between others, Ritchie puts stickers on his Poké Balls.