Pepper Ann sneaks out of detention and heads to the park, where she wins her first game of chess ever against a seasoned master.
Pepper Ann is stuck in detention and wants to experience the first day of Spring. While Vera is distracted, Pepper Ann sneaks out and winds up in the Chess Club room. There, the geeks lead by Alf, talk about their love of the sport, which Pepper Ann scoffs at. Alf challenges her to a game and to his surprise, actually gets beaten by her. When Pepper Ann leaves, Alf and the geeks all begin to find out who she is and discover the things she has done. Believing that she is a show off, Alf decides to challenge her again to another game.
Alf confronts Pepper Ann in front of her friends and challenges her to another game, surprising Nicky and Milo. When Alf accuses her of being a coward, Pepper Ann agrees and plays several games, all of them ending with her defeating him. Nicky concludes that Pepper Ann is a chess prodigy and they leave a humiliated Alf who still wants to play another game to regain his title. Alf follows her to Brain Dead, soccer practice and to the Freezy Pleezy all the while learning to do some of the things that she enjoys (like eating a sundae despite being lactose intolerant).
When Alf continues to pester Pepper Ann, she finally snaps and calls chess dumb, saddening him. Feeling bad for hurting his feelings, Pepper Ann heads back down to the Chess Club and is confronted by the other geeks for being rude. She apologizes and Alf arrives; admitting that ever since he followed Pepper Ann, he has learned that there is more to life than chess and has started to enjoy other things too. They play another game, but Alf wins this time, saying he was just lucky. Pepper Ann then begins to demand a rematch from him.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Shelf McClain, Craig Bean, Emit Swink
- Danny Cooksey as Milo Kamalani
- Clea Lewis as Nicky Little
- Pamela Adlon as Additional voices
- Paddi Edwards as Vera Groober-Schwartz
- Will Ferrell as Alf
- John Kassir as Geek 1, Geek 2, Video Game Voice
- Kathy Najimy as Coach Doogan
- Kath Soucie as A/V Geek Girl
- Cree Summer as Crying Girl
- On Disney+, the episode segment is first next to "Forging Ahead".
- In the credits, Emit Swink's name is spelled as "Emmett" Swink.
- The episode partially takes place on March 20, as Pepper Ann mentions that it is the first day of Spring.
- The title of the episode is a reference to the film Searching for Bobby Fischer, which is the film Pepper Ann keeps forgetting the name to.
- The chess team look into Pepper Ann's background and discover that she had a "bizarre trampoline incident", a reference to the episode "In Support of".