Woodson was drafted by the Oakland Raiders fourth overall in the 1998 NFL Draft. In his first season with Oakland, Woodson was selected as the NFL Defensive Rookie of the Year by the Associated Press. He was named to the Pro Bowl and earned All-Pro recognition three consecutive times (1999–2001). In a 2002 AFC playoff match against the New England Patriots, Woodson seemed to have clinched the game by forcing a fumble while sacking quarterback (and former Michigan teammate) Tom Brady, but the ruling was overturned. Woodson later battled several nagging injuries in consecutive seasons in Oakland, leading to his departure after the 2005 NFL season via free agency.