Crouch began his career as a trainee with Tottenham Hotspur. He failed to make an appearance for Spurs and after loan spells at Dulwich Hamlet and Swedish club IFK Hässleholm he joined Queens Park Rangers. After QPR were relegated at the end of the 2000–01 season, Portsmouth acquired him in a transfer deal worth £1.5 million. He had a strong first season at Fratton Park, and after scoring 19 goals for the club, he joined Aston Villa in March 2002 for £5 million. He had a relatively poor spell at Villa, however, and was loaned out to Norwich City in 2003 before making a move to Southampton, where he regained his form, which would ultimately prompt his joining Liverpool in July 2005. At Liverpool he enjoyed considerable success, winning the FA Cup and FA Community Shield in 2006, and also gaining a runners-up medal in the 2007 UEFA Champions League Final.