In October 2008, when Tottenham played away to Stoke, Vedran Ćorluka suffered an injury in the 77th minute. Dawson replaced him only to be sent off in injury time. In March 2009, Tottenham reached the League Cup final again and faced Manchester United. Dawson was available and was selected for the final which ended 0–0 after 90 minutes. However, Tottenham lost 4–1 on penalties. In April 2009, Dawson sustained an injury against Newcastle United which left him out for the rest of the 2008–09 season. The 2009–10 season was to be judged by many as Dawson's finest season in a Spurs shirt to date as he helped the club to a fourth-place finish, their highest league finish for 20 years and qualification for the 2010–11 UEFA Champions League.