• English / United States: Olesia's Wooper
• Japanese / Japan: サナエのウパー
• Japanese (Romanized) / Japan: Sanae no Upah
• Japanese (TL) / Japan: Sanae's Upah

Olesia runs a nursery school for Wooper where she also takes care of her own Wooper. Olesia's Wooper has a heart shaped marking on its chest which makes it easy for people to identify it from other Wooper. Olesia's Wooper is a very curious Pokémon that likes to explore on its own but often gets into trouble for doing so.

While on-route to Kogane City, Olesia's Wooper jumped up on Brock's neck and the two of then slid down the side of a cliff to Olesia's nursery school for Wooper. She apologized for her Wooper's behavior and explained that it's sometimes just unable to control itself.

After Brock agreed to watch over the Wooper for Olesia, Olesia's Wooper ended up getting separated from the Wooper group and when Ash Ketchum and Misty tried to get it, it kept running away. Eventually it ended up crossing a rickety old bridge and Ash's Pikachu had to chase after it while Ash Ketchum and Misty climbed up the bridge which had collapsed. Team Rocket tried to capture it after they realized their boss might find it soothing but Olesia's Wooper proved to be a lot stronger than it looked as its Slam attack took out Jessie's Arbok and James's Weezing. Brock wanted to know how Olesia had trained her Wooper to be so strong but she said there wasn't any special method only that the water in their pond was good for it.