With Sherwood unsettled in 1999 and having family and business links in Hertfordshire, George Graham paid a reported fee of £3 million to bring him to Tottenham Hotspur in the first week of February 1999. He made his debut for Spurs as an 87th-minute substitute for Mauricio Taricco in the 0–0 draw with Coventry on 6 February. He was cup-tied for their victory in the 1999 Football League Cup Final. Sherwood won a runners-up medal with Spurs in the 2002 League Cup Final, when they were beaten by his former club Blackburn.