Sheppard was born in Salisbury in December 1992. He was educated at Queen Elizabeth's School in Wimborne Minster.[1] Sheppard made his way up though age-group cricket for Hampshire,[2] and in early 2011 he toured Sri Lanka with the England Under-19 cricket team, making a single Youth One Day International appearance against Sri Lanka Under-19s.[3] At the end of the 2012 season, Sheppard signed a one-year contract for the 2013 season, having impressed for South Wilts at club level in the Southern Premier Cricket League.[2] During the 2013 season, Sheppard made a single appearance for Hampshire in a List A one-day match against a touring Bangladesh A team at the Rose Bowl.[4] In a match which Hampshire won by 9 runs, Sheppard was dismissed without scoring by Rubel Hossain in Hampshire's innings of 223, while with the ball he took the wickets of Marshall Ayub and Hossain, finishing with figures of 2 for 49 from nine overs.[5] Sheppard made no further appearances for Hampshire and was released at the end of the 2013 season, alongside Hamza Riazuddin, Michael Roberts, and Adam Rouse.[6] Returning to club cricket following his release, he left South Wilts in 2014 to join Ealing in the Middlesex County Cricket League.[7]