AFC Wimbledon Oakley joined
AFC Wimbledon at the age of eleven, and progressed through the youth ranks. On 15 February 2014, he was named as a substitute in a 1–0 league defeat at
Portsmouth. He signed a professional contract in May 2014, and scored just days later in the 2014
London Senior Cup final win over
Metropolitan Police. Oakley was ruled out of the opening two months of the
2014–15 season with a hamstring injury. On 7 October 2014, he marked his return in a 4–0 defeat to
Charlton Athletic in the
U21 Premier League Cup. On 1 November 2014, he made his
Football League debut as a late substitute in a 2–0 loss at
Northampton Town. On 30 October 2015, Oakley joined affiliate
Isthmian Premier Division side
Kingstonian on a one-month loan. He made his debut the following day, scoring in a 5–1
FA Trophy win at
Leatherhead. A grade two hamstring tear ruled him out for eight weeks and his loan spell was ended prematurely. In January 2016, Oakley suffered a broken ankle during a training session, ruling him out for the remainder of the
2015–16 season. On 19 July 2016, he made his first appearance after the injury in a pre-season outing at
Raynes Park Vale. On 8 November 2016, he made his first appearance of the season for the senior squad in a 2–0
EFL Trophy defeat at
Newport County. Making his debut in a 3–1 defeat at
Hampton & Richmond Borough, he scored his first goal for the club a week later in a 1–0
FA Trophy win at
Concord Rangers. He added his second of the season in the next round of the cup, completing the scoring in an 8–1 win over
Hythe Town. On 16 December 2016, Oakley's loan at Welling was extended by a further month. On 17 March 2017, Oakley joined
National League side
Maidstone United on a one-month loan deal.
Inverness Caledonian Thistle Oakley signed for
Scottish Championship club
Inverness Caledonian Thistle in July 2017. He scored his first goal for the club in a 4–1 friendly win at
Brora Rangers. He then scored his first competitive goal in Inverness's first game of the season, the opening game of the
Scottish League Cup group stages, a 3–0 home win against
Brechin City. He started in the following match, a 0–0 draw away at
Stirling Albion which resulted in a 2–0 penalty shootout a win for ICT, the lowest scoring penalty shootout in Scottish football. His second competitive goal for Inverness came in a 2–1 win away to
Forfar Athletic, although this wasn't enough to prevent them exiting the League Cup. On 30 December 2017, with Inverness down to ten men and losing 2–1 against bottom of the table
Brechin City, Oakley came on as a substitute and netted twice to give Inverness the win. On his
Scottish Cup debut, he scored a late goal in a 2–2 draw v
Dundee, earning Inverness a replay at home.
Hamilton Academical In January 2019, Oakley moved to
Hamilton Academical. On 27 February 2019, he scored the opening goal as Hamilton won 2–0 away to
Aberdeen, with the goal drawing comparisons to
Marco van Basten.
Pirin Blagoevgrad In June 2020, he signed a two-year contract with Bulgarian club
Pirin Blagoevgrad. In January 2021, he was training with
Kilmarnock after leaving Pirin.
Kilmarnock On 26 January 2021, after a trial period, Oakley returned to the Scottish Premiership with Kilmarnock after signing a deal until the end of the season. He left Kilmarnock at the end of the 2020–21 season.
Woking On 22 June 2021, it was announced that Oakley would join National League side,
Woking following his release from Kilmarnock. He went on to feature seventeen times, scoring once before leaving The Cards in July 2022 at the end of his contract.
Return to Inverness Caledonian Thistle On 2 July 2022, Oakley returned to
Inverness Caledonian Thistle, 3 years after leaving initially. A week later, Oakley scored on his second debut in a 1–0 away win over
Kelty Hearts in the League Cup. On 20 January 2023, Oakley left
Caley by mutual consent.
Greenock Morton On 24 January 2023, Oakley signed an 18-month contract with
Scottish Championship club
Greenock Morton. He scored his first Morton goal 4 minutes into his debut. Oakley would finish the season with 6 goals in 13 appearances, an average of roughly 1 goal every 2 games.
Ayr United In 2024, Oakley joined
Scottish Championship club
Ayr United on a two-year deal after previously signing a pre-contract agreement while at Morton. ==Career statistics==