The deal made Dempsey the highest salaried U.S. soccer player of all time. With the 23 shirt that he wore at Fulham and the number 8 that he usually wears on international duty unavailable, he opted for the number 2 jersey, more usually associated with the right-back, which he wore at Furman University. He scored his first and the eventual match-winning goal for Tottenham in a 3–2 win over Manchester United. It was the first time in 23 years that Tottenham had won at Old Trafford. He scored his second goal for Spurs in the 39th minute in an away game at Southampton in October. Dempsey's third and fourth goals were scored against Everton in an eventual 2–1 loss and a deflected effort against Reading on New Year's Day to help his Spurs side win 3–1. In the FA Cup 3rd round he scored a double against Coventry City.