Born in Whitby, North Yorkshire, Jackson began his career at Third Division club Scarborough, as a trainee in August 1997. He made his first-team debut for the club in a 4–0 win at home to Doncaster Rovers on 1 November 1997.
Jackson was born in Whitby, North Yorkshire and began his career at Scarborough, which played in the Third Division. He made his debut for the club in an away match against Doncaster Rovers with a score of 4–0 on November 1, 1997.