Pepper Ann worries about her femininity when she's chosen to be a placekicker for the school football team and the guys love her for being a tomboy, so she competes in a beauty pageant, which happens to be on the same night as the big game.
Pepper Ann is spotted by middle school football Coach Bronson who immediately approaches her with the prospect of joining his football team for the season. Despite her being the only girl in the team, she accepts. At first, the other players are against her, but quickly warm up to her abilities and even give her some pointers. After a string of successful games and bonding with the players, the team all make remarks towards Pepper Ann and call her "one of the guys", which does not sit well with her.
Pepper Ann approaches Milo and Nicky on if they see her as a girl. While Nicky tells her that it does not matter, Milo implicitly points out her tomboyish mannerisms, which upsets her. She decides to got to Lydia to help her get in touch with her feminine side and reels her with the prospect of making dresses for her. They go to see Margot LaSandre who puts Pepper Ann through training sessions to make her act more lady-like. Coach Bronson recognizes that Pepper Ann is going through some things, but reminds her that the game is next Friday. Pepper Ann returns home to learn that the pageant that Lydia entered her in is also going to be next Friday.
With no other option, Pepper Ann has Nicky and Milo help her go back and forth between the pageant and football game. Just as she is brought out to make the final kick, Bud, one of the players tells her that even if she misses, he liked playing beside her. Pepper Ann makes the kick and decides to give up on the pageant. She returns anyway to tell everyone about what she learned about her femininity and that she no longer cares what people think. While she loses the pageant, Lydia congratulates her and Bud invites her to join the guys to eat.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Dieter Liederhosen, Bob Lilywise, Additional voices
- Danny Cooksey as Milo Kamalani
- Clea Lewis as Nicky Little
- Pamela Adlon as Moose Pearson
- April Winchell as Lydia Pearson, Grandma Lillian
- Paddi Edwards as Vera Groober-Schwartz
- Don Adams as Principal Hickey
- Tom Wilson as Coach Bronson
- Kathy Najimy as Coach Doogan, Margot LeSandre, Nelly Lilywise
- Jason Marsden as Bud
- Milo mentions the events of "Manly Milo".
- Pepper Ann continues being the best soccer player since "Soccer Season".
- In this episode Coach Bronson tells Pepper Ann that the first woman to play American football in middle school was Eunice Guilliard in 1914. The character was made up with that actual title going to Donna Kay Johnson as late as 2015.