 In the New Year's Day fixture of 2009, Stuart scored with a header from a free-kick taken by Sam Sloma, to hand Grays a 3–1 victory over Ebbsfleet United.Following the departure of manager Wayne Burnett, Stuart took the role of assistant manager at Grays, alongside Stuart Elliott in late January 2009.He signed for Rushden & Diamonds in June 2009, reuniting with former Grays manager Justin Edinburgh, who described him as "a great leader".