 He had a trial with Conference Premier team York City in July 2009 and played in the first half of a 3–3 draw with Leeds United in a pre-season friendly.He went on to score York's second goal in a 2–0 victory over Hartlepool United.He was told to leave Matlock by manager Mark Atkins in October, who criticised Jackson's attitude and conduct after having a trial with York while still being contracted by Matlock.