He began his playing career at Oxford United in 1971, making 75 league appearances in four years at the club.
Fleming scored six goals in the 1978–79 relegation season, enough to make him the club's joint top-scorer (along with Glenn Cockerill, Mick Harford, and Gordon Hobson).
[1] He left Sincil Bank at the end of 1979–80 season, having scored 18 goals in 141 league and cup games at the club.
[3] Fleming joined Wollongong City in the Australian National Soccer League where he spent the next six years, amassing over a hundred appearances.
In July 1998, he was sacked as coach of Wollongong Olympic despite the club standing in equal fifth place of the league and also being a semi-finalist in the Bampton Cup.
[4] A week after departing Olympic, Fleming was appointed coach of Kemblawarra, taking over from Joe Coelho, who had been acting as player-coach since the sacking of Jim Dafkovski.