James Olayinka

Loan to Northampton Town In January 2020, Olayinka moved on loan to League Two side Northampton Town until the end of the season, making his debut in a 3–0 win over Scunthorpe United on 28 January. He helped Northampton Town to secure promotion to League One by winning the play-off final.

Loan to Southend United In October 2020 he joined Southend United on loan until January 2021. He scored his first goal for the club, and his first professional goal, in an FA Cup tie against Boreham Wood on 7 November 2020. On 1 February 2021, Olayinka extended his loan with Southend United to the end of the 2020–21 season.

Cheltenham Town He signed a two-year contract with Cheltenham Town on 1 September 2022. On 2 January 2024, manager Darrell Clarke announced that Olayinka had been made available for transfer. He was released by the club at the end of the 2023–24 season.

Waterford On 14 November 2024, it was announced that Olayinka would be joining League of Ireland Premier Division club Waterford ahead of their 2025 season. On 21 November 2025, it was announced that he would be departing the club at the end of his contract, having made 33 appearances and scored one goal in all competitions.

Derry City On 15 December 2025, League of Ireland Premier Division club Derry City announced that Olayinka would join the club on a free transfer ahead of the 2026 season, signing a two-year contract. On 9 July 2026 he scored Derry's second goal in a 3–2 defeat away to CSKA Sofia in the UEFA Europa League, the first European goal of his career.

Personal life Olayinka is of Nigerian descent.

Career statistics + Appearances and goals by club, season and competition

Division!!Apps!!Goals!!Apps!!Goals!!Apps!!Goals!!Apps!!Goals!!Apps!!Goals

2019–20 League One

38!!1!!1!!0!!1!!0!!3!!0!!43!!1 Waterford 2025 LOI Premier Division

Derry City 2026

Arsenal FA Community Shield: 2020