Born in Bromley, Ajiboye joined Brighton & Hove Albion as a scholar in 2015 and had a loan spell with Worthing in 2017.

[5][6][7] He made his EFL Trophy debut for Brighton & Hove Albion U21 on 29 August 2017 in a 2–0 defeat to Milton Keynes Dons.

[21] On 30 December 2022, Ajiboye was announced to have returned to Sutton United on loan until the end of the 2022–23, a deal becoming active from 1 January.

[23] On 7 November 2024, Ajiboye joined National League side York City on loan until January 2025.

[24] On 16 January 2025 Ajiboye joined EFL League Two club Newport County on loan for the remainder of the 2024-25 season.