Callum Shepherd took part in pony racing and rode out for trainers during school holidays, before leaving school after his GCSEs to become apprentice at Charlie Hills yard in Lambourn. Sporting prowess is in the blood for the Shepherd family, with brother Laird a golfer on the European Tour.   

In 2020, Shepherd took up the opportunity to become retained rider for the Gredley Family in Newmarket, which provided him with the chance to ride in his first Group 1 race and British Classic in the 2021 Oaks on Save A Forest. In May 2024, he achieved his first victory in a Group race when Seven Questions, trained by George Scott, won the Group 3 Palace House Stakes at Newmarket.  

Shepherd secured his first Royal Ascot success in 2024, when he partnered Isle of Jura to victory in the Group 2 Hardwicke Stakes, before winning the 2025 edition of the Czech Derby, on Miss Of Change.