39 - James Chester Profile

Born in Warrington, Cheshire, Chester began his football career with his local club, Winwick Athletic, where, at the age of five, he was already playing in the club's Under-9s team. At the age of eight, he joined Manchester United, and signed a trainee contract at the age of 16 in July 2005. He went straight into the club's under-18 team, making 17 appearances in the 2005–06 season. He also got his first taste of reserve team football on 21 February 2006, when he was named as an unused substitute for a 4–1 away win over Everton. He continued in the under-18 side in 2006–07, and scored his first goal in a Manchester United shirt on 9 December 2006, scoring the opening goal in a 3–1 away defeat by Manchester City. He made his debut for the reserve team on 15 February 2007, helping to hold Bolton Wanderers to a goalless draw. At the end of the season, he played in the teams for both the FA Youth Cup and Manchester Senior Cup finals. However, the teams lost both finals, losing to Liverpool on penalties in the former and to Manchester City in the latter.

In 2007–08, Chester cemented his place as a regular in the reserve team, making 24 appearances in all competitions as the team won both the Manchester Senior Cup and the Lancashire Senior Cup, and finished in third place in the Premier Reserve League North. His consistent performances and on-field leadership earned him the reserve team captaincy for 2008–09. At the start of the season, he was given a first team squad number – 39. 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.

On 2 February 2009, Chester joined League One side Peterborough United – managed by Alex Ferguson's son, Darren – on loan. He made five appearances for the Posh before returning to Manchester United on 2 March. Towards the end of the season, along with Tom Cleverley and Corry Evans, Chester was nominated by reserve team manager Ole Gunnar Solskjær for the Denzil Haroun Reserve Player of the Year award.