Oakley joined AFC Wimbledon at the age of eleven, and progressed through the youth ranks.[3] On 15 February 2014, he was named as a substitute in a 1–0 league defeat at Portsmouth.[4] He signed a professional contract in May 2014, and scored just days later in the 2014 London Senior Cup final win over Metropolitan Police.[5]
On 30 October 2015, Oakley joined affiliate Isthmian Premier Division side Kingstonian on a one-month loan.[9] He made his debut the following day, scoring in a 5–1 FA Trophy win at Leatherhead.[10] He managed just 12 minutes in his second appearance – a 1–0 victory over Enfield Town – before suffering from injury.[10] A grade two hamstring tear ruled him out for eight weeks and his loan spell was ended prematurely.[11]
In January 2016, Oakley suffered a broken ankle during a training session, ruling him out for the remainder of the 2015–16 season.[12] On 19 July 2016, he made his first appearance after the injury in a pre-season outing at Raynes Park Vale.[13] 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.[14]
On 18 November 2016, Now plays for woking his 21st birthday, Oakley joined National League South club Welling United on a one-month loan.[15] 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.[16] 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.[17] On 16 December 2016, Oakley's loan at Welling was extended by a further month.[18]
Oakley signed for Scottish Championship club Inverness Caledonian Thistle in July 2017.[20] He scored his first goal for the club in a 4–1 friendly win at Brora Rangers.[21] 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.[22] 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.[23] 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.[24]
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.[25]
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.[30] He left Kilmarnock at the end of the 2020–21 season.[31]
Woking
On 22 June 2021, it was announced that Oakley would join National League side, Woking following his release from Kilmarnock.[32] He went on to feature seventeen times, scoring once before leaving The Cards in July 2022 at the end of his contract.[33]
Inverness Caledonian Thistle (Second Spell)
On 2 July 2022, Oakley returned to Inverness Caledonian Thistle, 3 years after leaving initially.[34] 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.[35]
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.[36] 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.[37]
Career statistics
As of 24 January 2023
Appearances and goals by club, season and competition