Shepherd moved to Carlisle when he was sixteen and made a winning professional debut in 1991 against Chris Aston, and soon moved himself into a championship position by winning a series of bouts in his opponents backyard including against amateur star George Naylor in Liverpool, Southern Area Lightweight Champion Cham Joof in London, Midlands Area Lightweight Champion Karl Taylor and future WBO Light- Welterweight world title challenger Nigel Wenton.
This earned him a crack at Michael Ayers for the British Lightweight Championship in Potters Bar the following month which he lost in an all out war in 3 rounds against the future WBO World title Challenger.
Ultimately the setback convinced Shepherd to drop down to Super Featherweight and he returned at his new weight to destroy John Stovin in 4 rounds in December, and then he overcame a terrible cut to force a controversial stoppage against Swansea hard man Marc Smith at Crystal Palace in April 1996.
By July 1999 a match was made to fight the American Tom Johnson for the IBO World Title in his hometown of Carlisle where a tight victory was achieved in front of an adoring crowd.
However, in searching for a big payday against Naseem Hamed the decision was made to drop down to the featherweight limit in his first defence and a weight drained Shepherd was swept aside by Algerian-based Frenchman Affif Djelti in 6 rounds.