Career
Chesterfield
Born in Sheffield, South Yorkshire, Jackson started his career with Chesterfield after signing a three-year scholarship in 2003, before signing a two-year professional contract in April 2006. He made his first team debut after coming on as a 71st minute substitute in a 3–1 defeat to Portuguese Vale on 29 April. He had loans with Matlock Town and Gainsborough Trinity, where he made four appearances during the 2007-2008 season.
Matlock Town
He joined Matlock permanently in August 2008.
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. He later had his contract cancelled by the club
Worksop Town
In February 2010 he signed for Worksop Town, initially until the end of the season this was extended and he is still currently with the club
Bradford Park Avenue
In June 2012 Jackson joined Bradford Park Avenue. He joined Conference Premier club Football Club Halifax Town following a successful trial on 29 July 2014.
