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.

[3] He made his Football League debut against Everton in May 1987,[4] but struggled to gain a place in the first team, and was sent to Leyton Orient on loan in March 1988, where he played ten times.

[5] After Kevin Keegan took over as manager, however, Stimson found himself out of favour and he had a short spell on loan to Portsmouth in December 1992, which led to a £100,000 transfer at the end of that season.

[20] In the same season, Stimson also led Grays to the FA Trophy Final, where the team beat Hucknall Town in a penalty shoot-out.

[22] Grays reached the FA Trophy Final again in the following season, and claimed a second successive win after a 2–0 victory over Woking at Upton Park.

[23] In the Conference, Grays finished in third place and qualified for the play-offs for promotion to the Football League, but lost to Halifax Town in the semi-finals.

[25] He was linked with the managerial vacancy at League Two Peterborough United,[26] but eventually took over as manager of Stevenage Borough on 28 May,[27] and led the club to an eighth-place finish in the Conference National in his first season in charge.

[30] In the early part of the 2007–08 season, speculation began to mount that Stimson would be approached to take over as manager of a Football League club, with Gillingham, Port Vale and Millwall all alleged to be interested in his services.

[33] On 1 November, he was appointed as the new manager of Gillingham,[34] and quickly moved to sign a number of Stevenage players, including Adam Miller and John Nutter.

[36] He was also criticised by departing player Aaron Brown, who acknowledged that Stimson had strong coaching skills but described his man-management as "shocking".

[52] Stimson is married, and when he returned to former club Grays Athletic as manager of Stevenage Borough in 2007, he and his wife were praised for visiting the clubhouse after the game to chat to home supporters.

[53] He has three children, including a son, Charlie, who in 2008 joined Gillingham's youth team, but turned down the offer of a professional contract in 2010 after his father's dismissal from the manager's job.