Shepherd was a member of the Sparta Amateur Boxing Club in Edinburgh[2] and represented Scotland at international level.[3]
He represented the Scottish team[4] at the 1994 Commonwealth Games in Victoria, Canada, where he competed in the flyweight division.[5] At the Games he won the gold medal following victories over Tanzania's Matumla Mbwama, Nigeria's Enenuvwedia Osiobe, England's Danny Costello and finally Duncan Karanja of Kenya in the final.[6][7]
Following their successes at the Games, Shepherd and fellow boxer John Wilson were honoured by the Edinburgh community and local celebrities with a dinner on their behalf.[8]
A postal worker by profession, Shepherd became disillusioned with the sport and despite being selected for the pre-1996 Summer Olympics training squad he announced his retirement from boxing in February 1996.[9] Shepherd struggled with the fame associated with his gold medal and began drinking heavily and in 1998 received a 12 months jail sentence for driving under the influence of methadone.[1]