His first start for Tottenham came on 14 September 2006, away to Slavia Prague in the UEFA Cup, a match that Tottenham won 1–0. His first goal for Tottenham came in the League Cup fourth round match against Port Vale on 8 November 2006. Huddlestone scored two goals in this match, his second goal proving decisive in extra time, taking Tottenham through to the quarter-final of the competition. Huddlestone got his first league goal for Tottenham on 17 December 2006 against Manchester City with an excellent half-volley on 24 minutes, hit first-time after assisting with teammate Calum Davenport's first goal with a free-kick. Huddlestone established himself as one of the most promising young English central midfielders in the Premier League towards the end of the 2006–07 season and head coach Martin Jol compared Tom Huddlestone with German legend Franz Beckenbauer due to his playmaking abilities, ferocious shot power and versatility.