Originally Fleming was a trainee with Coventry City before moving on to play for both Northampton Town and Preston North End.
In the summer of 2000, The Imps lost Fleming to Plymouth Argyle with fellow central midfielder John Finnigan also departing that season.
With the club cash strapped [citation needed] though Fleming left United at the end of the 2003–04 season and joined Grimsby Town on a free transfer.
Terry was named as Grantham Town's captain for the 2008–09 season, impressing Gingerbreads manager John Wilkinson with his professionalism and experience.
[3] He joined Sleaford Town in a playing capacity, debuting in the club's 1-1 United Counties League draw at Yaxley on 27 April 2013.
[4] In June 2013 he was appointed player/assistant manager to Kris Jones at Sleaford Town with his one-time Lincoln City teammate Gavin Gordon as first team coach.
[10] On 13 February 2017 Fleming and manager Dave Frecklington left Spalding United to join National League North side Gainsborough Trinity.