Jimmy Simpson from Portsmouth was described in the Interlink Express Ultimate Book of Non-League Players" as a "diminutive yet powerful midfield player who is strong in the tackle and a good passer of the ball". Unfortunately for both Norwich City and for Jimmy, injury problems hindered his development just as he was about to break into the Canaries' first team squad.

He was released in 1995 at the age of 19 and joined Dr Martens league side Corby Town. He switched to rival Dr Martens side Raunds Town at the start of the 1996/97 season but moved on to Rothwell Town, also of the Dr Martens League, and then to Ford Sports

After returning to Corby, Jimmy joined St Neots Town of the United Counties League in early 1999. Another spell at Raunds Town preceded a move to Daventry before he signed for Banbury in August 2001. A spell at Ford Sports followed before he moved to Desborough Town in August 2004.