|Location:||Pier in Old Bullworth Vale|
- "Well, what have you tried so far?"
- "Random violence, widespread destruction, gratuitous sadism."
- "No, no that's not gonna work - they get all that kind of stuff at home."
- — Petey and Jimmy discussing subduing the Preps
Boxing Challenge is a mission in Chapter 2.
Jimmy and Petey are sitting on the end of the longest pier in Old Bullworth Vale. Jimmy is frustrated as nothing he's tried is cowing the Preppies. Petey points out that simple violence and abuse isn't enough because the Preppies get that at home, and what Jimmy needs to do is prove publically that he's better than they are. To this end he suggests that Jimmy challenge Bif Taylor to a boxing match.
The weather turns to light snow as Jimmy heads from the pier to the Glass Jaw Boxing Club. Inside, he challenges Bif, who accepts.
Bif fights the same way all the other opponents in the boxing minigame fight, and is no tougher than any of the others.
Once Jimmy wins, Dishonorable Fight starts automatically.
- Bif is the only boxing challenger to have his full name printed above his life bar. There is no reason behind this.
- The music when boxing Bif is slightly different than when boxing other Preppies.
- The preppies watching the match use unique chants favoring Bif during this fight, with the exception of Pinky.
- Pinky and Tad were watching the match, yet mysteriously vanish when Jimmy starts fighting the other Preppies.