[2] Fleming began his professional career with his hometown club Halifax Town (69 appearances, no goals) where he made his debut aged 16.
In this period, Manchester United manager Alex Ferguson described Fleming as "the best man-to-man marker in the country" after playing some memorable games against a young Ryan Giggs.
In 1993, he was involved in Oldham Athletic's great escape when they narrowly avoided relegation from the Premier League on goal difference.
To mark the fact that the 2006–07 season was his tenth with the club, Norwich City granted Fleming a testimonial match against Newcastle United which took place at Carrow Road on 26 July 2006.
In January 2007 Fleming joined Wolverhampton wanderers on a one-month loan deal and played once against {{subst:FcCardiff City}}.
[5] Fleming signed for non-league King's Lynn shortly after the start of the 2007–08 season, where he was under the management of former coach Keith Webb.
In this role he visits schools and other youth organisations to help encourage young people to achieve through hard work and dedication.