[2] 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[3] but his spell at the Racecourse Ground was dogged by injuries.
Three months later Bennett made the move to Dundalk where he rejoined forces with former teammates Ian Foster and Wayne Hatswell.
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.