For Spurs, the move brought a capable goal scorer (Dempsey finished fourth in goals scored in the 2011-12 season) into a team that was lacking strikers.
As for Dempsey, the move provided top competition and, most importantly, a new start after a messy breakup with Fulham.
Since then, though, the road has been rocky for Deuce at White Hart Lane.
So where does Dempsey stand after his first several matches at Spurs?
Let's analyze each of the American's Premier League and Europa League matches with the help of our friends at WhoScored.com.