Born in Plaistow in east London, Stimson played for the Essex county representative football team and was on the books of Queens Park Rangers, before joining Tottenham Hotspur on an apprenticeship in July 1984.
Prior to the 1999-2000 season, Stimson spent a short period on trial at another of his former clubs, Gillingham, but manager Peter Taylor decided against offering him a contract and he instead joined Isthmian League club Canvey Island [REF].