At the end of the 2000–01 season, Sheringham's four-year contract at Old Trafford expired. He was facing stiffer competition than ever for the places up front, most of all from United's new Dutch striker Ruud van Nistelrooy. He refused United's offer of a 12-month contract and returned to Tottenham on a free transfer as one of new manager Glenn Hoddle's first signings. In his first season back, Sheringham helped Tottenham to a ninth-place finish, the club's highest in 6 years, and to reach the League Cup final where they lost 2–1 to Blackburn Rovers, with Sheringham being brought down in the penalty area in the last minute for what he believed to be a penalty. 2002–03 brought a similar mid table finish, although Tottenham had topped the Premiership three games into the season. Sheringham made 80 appearances in all competitions for Tottenham in this period, scoring 26 goals.