On 21 June 2022, Headley, alongside Terriers teammate Josh Austerfield joined EFL League Two side Harrogate Town on loan for the 2022–23 season.[8] He made his league debut in the 3–0 win over Swindon Town on 30 July, then scored his first goal in the 2–1 defeat to Bradford City. He was recalled by his parent club in January 2023.[9]
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