Born in 1967, Stimson started his career in football at Tottenham Hotspur, earning a professional contract at the age of 18. He made just two appearances for the men from White Hart Lane, being loaned out for Leyton Orient and Gillingham in the process. A transfer to Newcastle United followed but he wasn't a regular there either, only playing 86 matches over four seasons, including a loan spell at Portsmouth.
That loan spell turned into a permanent move but his first taste of regular first team football failed to materialise, playing just 58 games in three seasons, again being loaned out, this time to Barnet. A move to Southend saw just 57 appearances in three seasons before he joined Leyton Orient, making just 4 appearances. Spells at Canvey Island and Grays followed before retiring from professional football, taking over the hotseat at Grays.
His spell there was a success. A 6th place finish in the Isthmian League in 2003/4 was enough to secure a place in the new Conference South. Grays dominated the division and won by a massive 23 points, achieving promotion to the Conference. That season also included a successful trip to the FA Trophy final, beating Hucknall Town on penalties.
The 2005/6 season saw highs and lows. Grays again won the FA Trophy by beating Woking at Upton Park. However, despite making 3rd place, Grays lost out in the Playoffs to Halifax Town. Stimson quit the Essex club and became manager of Stevenage Borough, finishing 8th in his only full season in charge, but also securing his third FA Trophy success in a row, beating Kidderminster Harriers 3-2 in the final.
He quite Stevenage just under a year ago and took over as manager of Gillingham in November 2007. The Gills gradually got pulled into a relegation battle and suffered relegation to League Two in Stimson's first spell in charge at the club.
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