Born in Bristol, Jackson joined League Two club Hereford United on an initial one-month loan on 21 August 2009, alongside his clubmate and fellow young striker Tristan Plummer. Jackson joined League Two club Aldershot Town on an initial one-month loan on 25 November 2009. Jackson joined AFC Telford United on loan in January 2012, and scored on his debut against Kettering Town at the New Bucks Head Stadium. He rejoined the club on loan for a second period in March 2012. At the end of the 2011–12 season, he was released from Bristol City.
After his release from Bristol City, Jackson joined newly relegated club Hereford United on a one-year deal. He scored on his début and Hereford's first game of the season in a 2–1 win over Macclesfield Town. Following this, in his second game for the Bulls, Jackson was sent off in the first half for violent conduct, in a match which saw Hereford draw 2–2 with Tamworth F.C.
On 31 July 2013 Jackson completed a move back to the Football League by signing for League Two club Bury on a one-year deal. Jackson scored his first goal for the club, coming on as a substitute, to score the third goal in a 3–0 victory against Accrington Stanley. On 16 January 2014, Jackson's contract was cancelled.
On 16 January 2014 Jackson signed for the Conference Premier club FC Halifax Town from Bury. He was released by Halifax in June 2014 and joined Oxford City.
On 29 August 2015 Jackson signed for National League newcomers Tranmere Rovers on a non contract basis. He was released by Tranmere in December 2014 and rejoined Oxford City.
On 27 July 2016 Jackson signed for League Two club Newport County on a one-year contract after a successful trial period. He made his debut for Newport on 6 August 2016 versus Mansfield Town. He scored his first goal for Newport in a 3–2 EFL Cup loss against Milton Keynes Dons on 9 August 2016. On the 18 May 2017 Jackson signed a one-year contract to remain with Newport County. He was released by Newport at the end of the 2017-18 season.
Hereford F.C.
On the 27 September 2018 it was announced his much rumoured signing at Hereford was completed and International clearance received. He made his debut the same day in an FA Cup draw against Truro City F.C. and scored his first goal for the club 3 days later in the replay.
