Fleming was born in Blairhall, Fife and joined East Fife from Blairhall Colliery and became an integral part of East Fife's success in the 1940s and 1950s.
Fleming's early life in Blairhall, Fife set the stage for his success as he joined East Fife from Blairhall Colliery and contributed significantly to the team's successes in the 1940s and 1950s.