Fleming made his debut for Wrexham in 2007 and claimed a regular place in the first team. He left Wrexham to sign for Morecambe on 27 July 2010 and made his debut for the club in a 2–0 win over Coventry City in the Football League Cup. He scored both goals and became the first player to score at Morecambe’s new stadium the Globe Arena. Fleming went on to score 18 goals for the club and became a first team regular. In May 2009, Fleming made his debut for the England C team in the 2007–09 International Challenge Trophy final, a 1–0 defeat against Belgium U21’s. He played again on 26 May 2010, scoring once in the 2009–11 International Challenge Trophy match versus the Republic of Ireland, which they won 2–1.
The agile midfielder has gone on to be a valuable member of the Morecambe squad making over 250 appearances, winning Player of the Season for his contribution in 2013/14 and signing a new deal for the 2018/19 season to take him into a ninth season with the League Two club.