Sinclair joined Bristol Rovers at the age of nine. He became the second-youngest Bristol Rovers first-team debutant – at the age of 15 years 277 days – as a late substitute for Junior Agogo in the League Two game against Leyton Orient in December 2004.
Chelsea signed Sinclair in July 2005. A Football League tribunal set the compensation to be paid to Bristol Rovers at an initial £200,000, with increments up to a potential £750,000 to be paid if and when the player met various appearance milestones at club or international level. Chelsea would also have to pay Rovers 15% of the profit on any future sale.
Sinclair was called up for Chelsea's squad to play Macclesfield Town in the FA Cup on 6 January 2007 but remained on the bench. His debut came four days later as a very late substitute in the 2007 League Cup semi-final against Wycombe Wanderers. He scored his first goal for Chelsea in September 2007, in the 37th minute of the League Cup Third Round against Hull City to help Chelsea win 4–0. He provided the assist for Frank Lampard's 100th goal for... Read More