Career
Having played for AFC Wimbledon since age eleven, Oakley first appeared for the Dons in the 2013-2014 season, as an unused substitute in the 1–0 away loss to Portsmouth on 15 February 2014. Oakley missed the first two months of the 2014-2015 season with a hamstring injury suffered in pre-season. He made his return from injury on 7 October 2014, in the 4–0 loss away to Charlton Athletic in the U21 Premier League Cup.
He made his Football League debut on 1 November 2014, coming on as a late substitute in a 2–0 loss at Northampton Town.
