He was first included in a matchday squad on 20 August 2013, in a Scottish Challenge Cup second round match at Ayr United, coming on in the 96th minute for Thomas Grant and heading the winner in a 2–1 win.
[1] He made his professional debut four days later in a 0–3 Scottish Championship win at Livingston, replacing hat-trick scorer Philip Roberts for the final 22 minutes.
[2] On 23 November, he came on as an 85th-minute substitute for Rory Loy, and two minutes later scored his first league goal to conclude a 4–0 home win over Cowdenbeath.
[3] On 2 August 2014, Shepherd scored four minutes after replacing Botti Biabi to conclude a 3–1 comeback win at Montrose in the first round of the Scottish Challenge Cup.
[7] Shepherd was loaned to Edinburgh City in November 2017,[8] with the move subsequently being extended until the end of the 2017–18 season.