In the 2007–08 season, Dawson scored his first goal in the UEFA Cup home match against the Greek team Anorthosis Famagusta where Tottenham won 6–1. In November 2007, Tottenham went away to West Ham United in the Premier League and drew 1–1, Dawson scored the away goal. During the course of the season, Tottenham reached the 2008 League Cup Final at Wembley Stadium, where they beat Chelsea 2–1 to earn Dawson his first ever silverware, though he missed the final through injury.