Jaheim Anthony Headley (born 24 September 2001) is an English professional footballer who plays as a left-back for EFL League Two club Port Vale.
Headley spent time in the youth team at Millwall, then joined Huddersfield Town's under-17 squad via the Mass Elite Academy.
[4] On 2 August 2019, Headley and teammate Isaac Marriott joined National League North club Bradford (Park Avenue) on a work experience loan after impressing Garry Thompson on trial.
[10] On 30 October 2020, Headley and teammate Mustapha Olagunju joined National League South side Welling United on a three-month loan deal.
[18] On 21 June 2022, Headley, alongside Terriers teammate Josh Austerfield joined League Two side Harrogate Town on loan for the 2022–23 season.
[19] Management duo Simon Weaver and Paul Thirlwell had identified him as a "very dynamic and powerful left-back" who would be hard for the opposition to handle.
[22] Loan manager David Fox recalled him to Huddersfield on 9 January after Headley claimed two goals and two assists from 25 games for Harrogate.
[25] Eleven days later he scored his first goal at the Kirklees Stadium in a 2–1 victory over Birmingham City in what was manager Neil Warnock's first win in his second spell at the club.
[33] Headley sustained an ankle injury on New Year's Day and was left out of action for two months as a result, regaining fitness just as André Breitenreiter was installed as the club's new manager.
[38] On 2 January 2025, Headley joined League Two club Port Vale for an undisclosed fee on a two-and-a-half year deal, the move seeing him reunite with former Huddersfield Town manager Darren Moore.