Dave Flemming began his career at Luton Town on YTS terms. He played twice for the Norwich City Reserves in season 1991/92. He then spent time in North London with Leyton Orient and Enfield before moving back to East Anglia, joining Harwich for whom he scored regularly. Since July 1997, his career has taken a nomadic twist with spells at non-league sides Bromley and Kingstonian followed by a return to the Eastern Counties League with Felixstowe. Dave then signed for Wivenhoe Town of the Ryman League Division Two for whom he made 24 appearances (1 as substitute) in the 1997/98 season scoring eight goals. He later played for Clacton and Sudbury Wanderers.

According to local papers in the Enfield area in the summer of 1999, Enfield have first option on his signature if he chooses to return from France where he has been playing recently for Dunkirk. Dave trained with and played for Enfield in a number of pre-season friendlies in July/August 1999. The Rymans League website reported on December 13th 1999 that Dave had transferred from Romford to Carshalton Athletic
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Dave returned to Enfield in July 2000 playing on trial for the Es in their 2-1 friendly defeat at home to Orient and then in the initial matches of the 2000/01 campaign. Dave moved to Hemel Hempstead Town in March 2001 but was linked with a move back to EN1 to join the newly formed Enfield Town FC. However he instead joined Welling in August 2001. Dave moved on to Arlesey Town in December 2001 but quickly moved to Folkestone Invictia the following month. According to the Non League Paper website that reported Dave's move to Folkestone, he has also played for Crystal Palace, Lincoln, Southend and Kettering, After a brief spell with Arlesey, Dave moved to Horsham in February 2002 and to Fisher Athletic in August 2002. He returned to Horsham before joining St Leonards in September 2003. He is believed to have also played for Redhill.