Career
Born in Wolverhampton, Bennett, who was a junior at Aston Villa, made one appearance for West Bromwich Albion while at the Hawthorns in 1996–97.
Dean was signed by Chester City from Wrexham in 2006, he has also played for Kidderminster Harriers (where he won the Conference National in 1999–2000) and Bromsgrove Rovers.
In 2004–05, Bennett was part of the Wrexham side that won the Football League Trophy against Southend United at the Millennium Stadium but his spell at the Racecourse Ground was dogged by injuries. This has continued at Chester, where he has missed the early weeks of the 2006–07 season. In August 2007, Bennett returned to former club Kidderminster on a three month loan deal. and he went on to spend almost the whole campaign with the club. At the end of the season, he was released by Chester, before returning yet again to Kidderminster. Dean stayed at Kidderminster until May 2010.
Three months later Bennett made the move to Dundalk where he rejoined forces with former teammates Ian Foster and Wayne Hatswell. He made his debt at home to UCD, on 6 August. He went on to make 13 appearances in 2010. His 2011 season was been disrupted by injury. Bennett scored his first competitive goal for the club with a header against Galway United in the FAI Cup at Oriel Park on 5 June.
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