On 26 January 2009, Chimbonda underwent a medical at Tottenham Hotspur ahead of a proposed return to White Hart Lane and the deal was completed the following day. Sunderland manager Ricky Sbragia declined to reveal the fee, although it is thought that Sunderland would recoup what they originally paid for Chimbonda, somewhere around the £3 million mark. His second Tottenham debut came in a 3–2 defeat against Bolton Wanderers on 31 January, where he set up Darren Bent to pull one back for Spurs, after coming on as a substitute. He was cup-tied for Spurs' appearance in the 2009 Football League Cup Final. During this second spell with Tottenham he appeared in 5 games in all competitions including playing in three league matches, and the other two matches he featured in were in the UEFA Cup.