And so it proved. After failing to displace the likes of Frank Lampard, Michael Ballack or Michael Essien from the the Blues' midfield, Sidwell decided to move to Aston Villa where he has the chance of more first-team action.
As a teenager, Sidwell was an Arsenal midfielder who struggled to make the breakthrough into the first team.
The player was loaned out to Second Division side Brentford in October 2001 for the remainder of the season and he would become an integral member of the side which just missed out on promotion in the play-offs.
On his return to Arsenal he was soon sent out on loan again, this time to the Gunners' Belgian feeder club Beveren. He only spent a couple of months there before returning to England and landing a temporary switch to struggling First Division side Brighton & Hove Albion.
Sidwell was a real star for the south coast club, but he was snatched from them in January 2003 when Reading signed him for an undisclosed fee.
After a great first season, the England Under-20 international was voted as the best player outside of the Premier League by FourFourTwo Magazine in 2004.
A vital part of Reading's Championship-winning 2005/06 squad, Sidwell was named in the Championship Team of the Year in April 2006 and continued to raise eyebrows with his consistent level of performance.
His calmness on the ball, ability to pick the killer pass and general energy in the centre of the park made him the pick of a Reading side which remarkably finished in the top half of the table. Numerous clubs were tracking Sidwell before it was announced he would join Chelsea for 2007/08.
Sidwell stated that he had not come to Chelsea to 'make up the numbers', but he did not manage to break into the first-team during his year at the club.
Without a chance of regular football, Sidwell opted to join Villa in summer 2008 and signed for the club for a fee of around £5million.
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