Born in Whitby, North Yorkshire,[1] Jackson began his career at Third Division club Scarborough, as a trainee in August 1997.

[1] He did not feature for the club until making successive appearances in the final two matches of 1999–2000, including his debut for Derby in a 0–0 draw at home to Newcastle United on 6 May 2000.

[11] He made 20 appearances in 2004–05, until he suffered a groin injury in a match against Leeds United in January 2005, which ruled him out of first-team action until May as Derby reached the Championship play-offs.

[17][18] By this time, Jackson was the longest serving player at Derby and, on 26 January 2006, signed a contract keeping him at the club until the summer of 2008.

[20] Jackson moved to newly relegated League One club Luton Town on a free transfer, signing a two-year contract on 8 August 2007.