On 25 December 2006, he signed a new four and a half-year contract – keeping him at the club until 2011. Tom signed a new and improved five-year contract on 30 June 2008 committing his future to Tottenham until 2013. He came on as a substitute as Tottenham beat Chelsea in the 2008 League Cup Final at Wembley Stadium. During the 2009–10 season, he became a regular under Harry Redknapp. In March 2010, he extended his contract until 2015. Huddlestone was plagued with injury during the 2011–12 season and managed only four appearances for the club. Huddlestone returned for the 2012–13 season and made his first appearance as a substitute for Jermain Defoe against Norwich City on 1 September 2012. He was shown a red card for serious foul play, the match ended in a disappointing 1–1 draw. The red card was later rescinded.