Stringfellow began his career with Mansfield Town in 1985. He remained with the Stags for nine years, making 163 league appearances and scoring 28 goals.
In January 1992 he joined Billy Ayre's Blackpool on loan. In his three games for the Seasiders he scored one goal, in a 2-2 draw with Brighton & Hove Albion at Bloomfield Road on 19 September 1992, with Trevor Sinclair scoring the hosts' other goal.
He also went on loan to Chesterfield the following season, before making a permanent move to Cambridge City, with whom he remained for four years.
In 1998 he joined Kettering Town, and two years later moved to Boston United.
In May 2000 he joined Dr Martens League side Wisbech Town as player-manager; however, he was sacked on 19 November 2000, after a 7-0 defeat at Rothwell Town.
Stringfellow finished his playing career with Bury Town in 2003.