He also appeared in Super Bowl XXXVII while a member of the Raiders during the 2002 season. The team went on to lose the game 48-21 to one of Upshaw's former teams, the Buccaneers.
The Tampa Bay Buccaneers selected him in the first round with the 12th pick overall in the 1996 NFL Draft. He later played for the Jacksonville Jaguars, Oakland Raiders, Washington Redskins, and New York Giants.