On January 20, 2013, in driving snow at White Hart Lane against league leaders Manchester United, Dempsey was able to salvage a dramatic 1–1 draw for Spurs by slotting home a pass from Aaron Lennon in the 93rd minute. The goal was his fourth in four appearances in 2013. On January 27, 2013, Dempsey scored a looping header against Leeds United at Elland Road, in the FA Cup to bring the score to 2–1, however Tottenham Hotspur couldn't draw level throughout the rest of the game, leaving the result at 2–1 to Leeds at the whistle.