Jackson joined Milton Keynes Dons' academy at a young age, progressing through various age groups and into the club's development squad. On 7 May 2016, Jackson made his debut for the first team, featuring as a substitute in the 88th minute in a 1–2 home defeat to Nottingham Forest.[3] On 26 July 2016, following an impressive spell in pre-season, Jackson signed professional terms with the club signing a one-year deal with an option of a further 12 months.[4]
On 17 February 2017, Jackson joined National League South side Hemel Hempstead Town on a youth loan deal until the end of the 2016–17 season, eventually making 4 appearances for the club.[5] On 14 June 2017, Jackson's contract was extended until summer 2018 and later again until the summer of 2019.[6] However, following limited first team opportunities, Jackson was one of ten players released by the club at the end of the 2018–19 season.[7]
ÍBV
On 18 July 2019, Jackson signed for Icelandic Úrvalsdeild club ÍBV.[8]