 On 13 March 2014, Bennett joined League Two side Chesterfield on a month's loan.On 9 April 2014 he was recalled back to Derby.After returning to Derby County on 9 April, Bennett was left out of the squad that faced Queens Park Rangers in the 2014 Football League Championship play-off Final but later signed a new four-year deal on 29 July to secure his future at the club.