He attended Thomas Telford School, where he captained the football team to win the County Cup 5 years in a row. Bennett was also a talented 200m sprinter and represented Shropshire at the English School Athletics Championships. He left school to gain a Scholarship at Wolves alongside Lee Collins, and signed professional forms with them in March 2007.
The midfielder has never made a league appearance for the club though, despite being picked for the first team squad several times, but has appeared in the League Cup. He made his professional debut on 15 August 2007 in a 2–1 win over Bradford City in the first round of that season's competition.
He was loaned to League One club Crewe Alexandra in November 2007 for two months and made his league debut on 3 November 2007, in a 2–0 win over Yeovil Town. He scored his first goal in only his second game to give Crewe a 1–0 success at rivals Port Vale.
His association with the Shakers will continue again during the 2008/09 season as he will spend the first half of the campaign on loan again with them.