A ball-playing centre-half, Shepherd played non-League football with Penistone Church, Athersley Recreation and Pontefract Collieries, before turning professional with Barnsley in July 2023.

Shepherd played Northern Counties East League football for Penistone Church (over two spells) and Athersley Recreation.

[6] He reverted to centre-half and earned comparisons to Paolo Maldini by Colls supporters as he scored three goals during some impressive performances during the 2022–23 season.

[9] On 4 July 2023, Shepherd signed with EFL League One club Barnsley after impressing Academy Manager Bobby Hassell on trial.

[11] He made his first-team debut on 5 August 2023, coming on as a substitute in a 7–0 win over Port Vale at Oakwell, in what was the biggest opening day defeat for any team in the English Football League since the 1962–63 season over 60 years ago.