Career
Born in Streatham, London, Jackson progressed through the youth system of AFC Wimbledon and joined the reserve team in 2008. In April 2010, Jackson signed a full-time contract after a man-of-the-match display against Tamworth in his first start for the club On 10 September 2011, Jackson made his Football League debut in a 1–1 draw with Aldershot Town, coming on as a substitute.
On 14 October, Jackson joined injury-hit Conference Premier side Fleetwood Town on a one-month loan.
On 31 January 2012, Jackson joined Cambridge United on loan until the end of the season. He was released by Wimbledon at the end of the season when his contract expired.
On 7 June 2012, Jackson signed for Macclesfield Town, dropping one tier to return to the Conference National. In July 2013, he signed for newly promoted Football League Two side Newport County on a free transfer.
In May 2015, Jackson turned down a new contract offer at Newport and signed for Football League One side Gillingham on a two-year contract.
He was signed by Gillingham manager Justin Edinburgh who had previously signed him for Newport County. Jackson was called up to represent the England C team in January 2013, for the International Challenge Trophy semi-final tie against Turkey U23s. He then earned another call up to the England C national team in June 2013, Jackson played the full 90 minutes in a 6–1 victory over Bermuda to earn his second cap.