Shepherd played Northern Counties East League football for Penistone Church (over two spells) and Athersley Recreation.[3] He was voted Wentworth Pewter Player of the Month at Penistone in October 2020.[4] He joined Pontefract Collieries in the Northern Premier League Division One East in September 2021.[5][6] He made his debut for Pontefract playing at left-back against Yorkshire Amateurs in the FA Trophy.[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.[6] He signed contract extensions in March 2022 and March 2023.[7][8] He won the club's young player of the season for two consecutive years.[9]
Barnsley
On 4 July 2023, Shepherd signed with EFL League One club Barnsley after impressing Academy Manager Bobby Hassell on trial.[10] Barnsley agreed to play Pontefract in a pre-season friendly as part of the deal, whilst agreeing to a "significant sell on clause".[6] Shepherd quit his job as a kitchen-fitter to turn professional.[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.[12][13]
Shepherd then made his first league start for Barnsley in an impressive 2-0 win away at Wigan on 26 August 2023.