Started his career as a youth at Tottenham Hotspur, where he made one appearance in the Premier League. Jamie was loaned out twice whilst at Spurs, to Danish side AB in 2004 and to Swindon Town in 2005. He then dropped down into non-League football signing a short-term contract with Aldershot Town in April 2005 until the end of the 2004–05 season. The following season he moved to Grays Athletic, before joining Oxford United on loan in November 2006. Jamie moved to Stevenage Borough in January 2007, staying for five months before joining Havant & Waterlooville the following season. He returned to Grays Athletic and had spells at Woking, Eastleigh, Chelmsford City then Sutton United, where he scored 14 goals in 31 appearances during the 2013-14 season before moving to Bromley where he featured prominently in their Conference South championship win. Signed for The Tudors in the summer of 2015.