Benn began his career at Bradford City before he signed for local rivals Bradford Park Avenue in 1995, upon his release from City. He was a very consistent and creative performer whether as a sweeper or in central midfield in over 400 games for the club. He had a spell on loan at Halifax Town before returning to Avenue in September 1996. He was player of the season in 1998-99. He left on a permanent basis in January 2004, signing for Frickley Athletic. In November 2004 he left for Emley before moving to Ossett Town in the Unibond Premier League.
Benn took over as manager of South Kirkby Colliery in July 2010, prior to this he was the assistant manager at Guiseley and Bradford Park Avenue. He left South Kirkby Colliery at the end of the 2010-11 seasons and was since appointed Manager of Hemsworth Miners Welfare, who play in the Northern Counties (East) League. Next Benn moved on to become manager at Goole AFC in the Evo Stik League.