Cork joined the Chelsea youth system up age of nine, and captained both the club's youth and reserve teams. During the 2006–07 season, Cork twice went on loan to League One club AFC Bournemouth. Cork was selected to go on Chelsea's pre-season tour of the United States in summer 2007. He made his first appearance for the first team against Club América on 14 July. He played out-of-position at left back for most of the tour.
Cork spent the 2007–08 season on loan at newly promoted Championship club Scunthorpe United. His first league goals came for Scunthorpe, both against Coventry City; in a 1–1 away draw on 27 November 2007 and in a 2–1 home victory on 1 March 2008. After 35 appearances, despite Scunthorpe's relegation from the Championship, he was voted the club's Player of the Year.
Cork has represented England at many youth levels, making his under-19 debut against the Czech Republic in May 2007. He captained the England U19 squad to make the 2008 UEFA European Under-19 Championship, and was part of the under-21 squad at the 2011 UEFA European Under-21 Championship.