Oran joined MK Dons academy at a young age, progressing through various age groups and into the club’s development squad. He made his debut for the first team on 7th May 2016, featuring as a substitute against Nottingham Forest. Following an impressive spell in pre-season, Jackson signed professional terms with the club. He made four appearances on loan at Hemel Hempstead Town in the latter stages of 2016/17 season. He remained on MK Dons books until summer of 2019 however, following limited first team opportunities he was released by the club at the end of that season. His football career then took an unusual route as he moved to Iceland to play top tier football for ÍBV making nine appearance in the early part of the season. Moving back to the UK he played for Billericay Town in the National League South and now brings his undoubted ability to Westwood Road to strengthen the Ives back line.