Originally with Scottish side Hearts, he signed for Manchester United on his 16th birthday.
He was released by United in the summer of 2009 without breaking into the first-team and returned to Scotland with Hibernian.
He went on to make fifty-two appearances for Hibs and the spent a year in Ireland with Limerick before joining Gillingham in December 2014.
The attacker joined the Minstermen on a free transfer in November 2015 and went on to make twenty-one appearances last season, scoring his one and only goal in a dramatic 2-1 home win against Stevenage in January.
The 25-year-old has penned a one-year deal to extend his stay in North Yorkshire.