Steve Sidwell is a London boy whosigned for Arsenal at a young age. The midfielder joined the Gunners at the age of 9 and he went on to win both the 2000 and 2001 FA Youth Cup titles. Steve Sidwell and James Harper played together in the Arsenal youth team and they went on to play together again at Reading.

Arsenal sent Steve Sidwell on loan to fellow London team Brentford at the start of the 2001/02 season in a bid for him to gain valuable first-team experience. He scored four times for Brentford in 35 games. Sidwell was part of the Brentford squad that lost 2-0 to Stoke City in the Championship playoff final. After a relatively successful loan spell at Brentford, Sidwell was sent on loan to Beverenin the Belgian league where he spent just a few weeks before returning to England.

Steve Sidwell left Beveren toreturn to English football after he was unable to secure a place in the first team during preseason. The midfielder joined Brighton and Hove Albion on loan for the 2002/03 season and he went on to score five goals in 12 appearances for the Seagulls. Brighton wanted to sign the player on a permanent deal during the winter transfer window in 2013 and they had a bid turned down by the Gunners. During the same winter transfer window, Arsenal also rejected a bid from Stoke City. In the end, Reading had an offer accepted for Steve Sidwell in the same transfer window.

Sidwell moved to Reading from Arsenal on a permanent deal for an undisclosed fee in January 2003. The midfielder penned a four-and-a-half year at Reading until the summer of 2007. His Reading debut ended in defeat. He played his first game for the Royals during the 3-1 defeat to Leicester City on January 29, 2003. In his second game for Reading, Steve Sidwell scored a brace in the 5-2 win over Burnley. The Arsenal Academy graduate made 15 appearances for Reading during the 2002/03 season as the Royals reached the playoffs before losing out to Wolverhampton Wanderers.

Steve Sidwellsigned for West London giants Chelsea on a free transfer after his Reading contract expired.