guppy was spotted playing for his local team, colden common and offered a chance with southampton in march 1989. he made a handful of appearances in the saints reserves at the end of the 1988–89 season (but failed to break into the first team) before moving to jim kelman's wycombe wanderers in september 1989. he turned professional with wycombe in 1992, at the age of 23. prior to turning pro he worked on building sites.