Fleming was born on 27 September 1986, in Dunfermline, Fife, Scotland. He attended Dunfermline High School where Craig Wilson was in the same year group. Fleming started his career with Livingston as part of the youth system, but he did not make a first-team appearance. He signed for Gretna in the summer of 2005. Fleming started to become a first-team regular during Gretna's only season in the Scottish Premier League. During October 2007, Fleming's contract was extended by Gretna and he was selected by the Scotland Under-21 side. On 19 May 2008, however, Fleming was part of the remaining 40 staff members who were released by Gretna due to their severe financial problems. He was not out of work long as Oldham Athletic signed him to a three-year contract on 21 May. He joined Dunfermline Athletic on a one-year loan deal in July 2009. In July 2010 he was transfer-listed by the club, along with five other first team players. On 31 January 2011, Fleming was released by Oldham Athletic. Fleming found a new club, signing for Galway United on a deal until the end of the season. On 29 July 2011 he signed a 12-month contract to be Tommy Lee's understudy at Chesterfield. He was released by the club in May 2012 after not being offered a new deal. On 21 July 2012 Fleming joined Grimsby Town on trial and played in the club's 0–0 draw with Hull City. 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. 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. Fleming was released by Grimsby on 3 May 2013. In July 2013 Fleming joined Workington on trial. Having played against Carlisle United for Workington he earned a trial with Carlisle United. On 2 August 2013, he signed a short-term deal with the club before being released at the end of the season. On 17 June 2014, Fleming signed for Carlisle's Northern League side Celtic Nation. Fleming signed for Scottish League One club Stenhousemuir on 15 August 2014, having been released by Celtic Nation following their financial problems. He made his debut the following day, in a 1–0 defeat against Brechin City. After just one season with The Warriors, Fleming transferred to Scottish League One rivals Ayr United. 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. 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. Fleming subsequently signed with Scottish League Two side Peterhead.
