[9] On 9 November 2019, Holness scored Darlington's first goal as they held League Two side Walsall to a 2–2 draw in the first round of the FA Cup.

[10] He also scored the winner as Darlington beat National League team Solihull Moors 1–0 in the FA Trophy first round replay.

[12][13] Holness rejoined Darlington on 16 October 2020 on non-contract terms,[14] and played in 11 matches, 7 in cup competitions and 4 in the National League North, whose season was again ended early because of the COVID-19 pandemic.

[16] His first goal for the club, an 82nd-minute header, secured an FA Cup second qualifying round win against ninth-tier opponents Shaftesbury.

[18] On 25 June 2023, Holness signed a professional contract with Ykkönen side FF Jaro, scoring his first goal for the team three weeks later against HIFK in a 3–0 win at Jakobstads Centralplan stadium.

Holness signed for Northern Premier League Division One West club Hednesford Town in July 2024.