Born in Greenwich, Greater London, Medley joined the youth academy at Chelsea when he was eight years old.[3]
Arsenal
Upon leaving Chelsea, he joined the youth academy at Arsenal in December 2016.[4] He captained the Arsenal under-18's at the beginning of the 2017–18 season before moving to the under-23 side.[3]
On 22 October 2018, Medley appeared on the bench for the Arsenal senior side for the first time in a Premier League match against Leicester City.[5] A month later, on 29 November, Medley made his senior competitive debut for Arsenal in the Europa League against Vorskla Poltava, coming on as a 60th-minute substitute for Rob Holding.[6]
Loan spells
Medley had joined League One club Gillingham on a season-long loan on 10 August 2020, becoming their fourth signing of the summer.[7] On 5 September, he made his debut in a 1–0 win against Southend United in the EFL Cup.[8] He made a total of 18 appearances for the club before he was recalled on 1 February 2021.[9] He immediately joined Scottish Premiership side Kilmarnock on loan until the end of the season.[10] On 6 February, he made his debut in a 2–0 loss against St Mirren in the Scottish Premiership.[11] On 27 February, he scored his first goal for Kilmarnock in a 1–1 draw against Dundee United in the Scottish Premiership.[12][13]
KV Oostende
On 21 June 2021, Medley joined Belgian First Division A side KV Oostende on a permanent deal, signing a four-year contract with the option of an additional year.[14]
Fleetwood Town
On 2 July 2024, Medley returned to England, signing for League Two club Fleetwood Town on a two-year deal.[15] In August 2024, he underwent surgery following a ruptured achilles,[16] returning to playing with the club's Development Squad in March 2025.[17]
On 29 January 2026, Medley joined League Two leaders Bromley on loan until the end of the season.[18]
On 15 May 2026, Fleetwood announced he would be leaving in the summer when his contract expired.[19]
International career
Born in England, Medley is of Jamaican descent.[20] He is a youth international for England.[21]