[5] The 2005–06 season saw Bennett managed to remain in the first team in the defence until he received a straight red card for a reckless tackle on Dani Rodrigues, in a 0–0 draw against AFC Bournemouth.
[7] After serving a three match suspension,[8] Bennett scored his first goal of the season one week later on 8 October 2005, in a 1–1 draw against Milton Keynes Dons.
[9] He made a total of over 50 appearances for Walsall, playing at centre-back and left-back[10] On 10 January 2006, Bennett signed for his home town club of Nottingham Forest in a two-and-a-half-year deal for an undisclosed fee.
[13] Four days later on 14 January 2006, Bennett made his Nottingham Forest debut, where he played 90 minutes, in a 3–0 win over Oldham Athletic.
[19] Manager Colin Calderwood did not play Bennett regularly earlier in the 2006–07 season, however he eventually established himself as Forest's first-choice left full-back.
[20] He received praise from Calderwood[21] after assisting both of Forest's goals in a 2–0 win against Tranmere Rovers, who admitted it would be difficult to take him out of the team despite Lockwood nearing a return.
[22][23] On 14 January 2008, Bennett signed a new 2+1⁄2-year contract, committing him to the club until the summer of 2010[24] On return to fitness, he managed to dislodge Matt Lockwood from the starting line-up and continued in the same vein of form.
[29] However, having established himself as first choice left-back at Forest and become a fan favourite – owing to his consistent form, local credentials and no-nonsense playing style – the rest of his career at the City Ground was ravaged by injury.
[32] Then, soon after his return, in December 2008 he sustained a serious knee injury (cruciate and cartilage ligaments) in the Boxing Day 4–2 home defeat to Doncaster Rovers.
[39] He did not play for the Forest first team for the entirety of the 2009–10 season, but he did make a minor public comeback at the final home match when he warmed up on the pitch with his teammates before the game.
[41] It was announced on 6 August 2010 that Bennett was allowed go on loan to Crystal Palace,[42] thus giving him the chance to demonstrate his match fitness and form through the improved opportunity of regular first team action.
Although Forest indicated they were prepared to offer Bennett a one-year contract should he be unable to find another club (in recognition of the community work he had undertaken during his time recovering from injury),[45] he subsequently signed for League One side Sheffield Wednesday.
Bennett made his Sheffield Wednesday debut, in the opening game of the season, where he set up a goal for Rob Jones to score a header, in a 2–0 win over Rochdale.
[64] After making four appearances, it was announced on 29 November 2012, his loan was cut short due to a back injury, and he returned to his parent club.
[65] Following this, Bennett never played again and at the end of the 2012–13 season, he was not offered a new deal as manager Dave Jones began his clear-out and his contract was about to expire.