[2][3] On 19 May 2008, however, Fleming was part of the remaining 40 staff members who were released by Gretna[4] due to their severe financial problems.
[10] On 21 July 2012 Fleming joined Grimsby Town on trial and played in the club's 0–0 draw with Hull City.
[11] On 24 July 2012 he accepted an offer from Grimsby and signed a one-year contract to compete with the club's first choice keeper James McKeown.
[12] Despite being handed the number 1 shirt for the season Fleming become the second choice at Blundell Park and didn't make his league debut until 22 January 2013 in a 2–0 victory over Hyde United.
[17] Fleming signed for Scottish League One club Stenhousemuir on 15 August 2014, having been released by Celtic Nation following their financial problems.
[20] Since signing for Ayr United, Fleming has saved 12 out of the 14 penalties he has faced, including 3 from 4 in the 2015–16 Scottish Championship play off win over Stranraer.
[citation needed] Following Ayr's relegation back to Scottish League One, and their decision to become a full-time club from the beginning of 2017–18 season, Fleming departed Somerset Park in June 2017 due to work commitments that meant he would be unable to train and play with the club on a full-time basis.