In July 2007, Chester signed his first professional contract with United. After being named as a substitute for the first team's 1–0 win over Bolton Wanderers on 17 January 2009, Chester was again selected as a substitute for the League Cup semi-final second leg against Derby County. With United 3–0 up at the time, Chester came on as a 67th-minute substitute for Gary Neville. Although Derby pulled two goals back, United ended up winning the match 4–2, meaning that they won the tie 4–3 on aggregate and qualified for the 2009 League Cup Final.