 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.