Cowell's father rode in Point-to-point races and bred racehorses including Untold. Cowell began his racing career working for Gavin Pritchard-Gordon. He also worked for John Hammond in France and Neil Drysdale in the United States before starting his own training career in 1996 at Hollywood Park Racetrack in California. In 1997 Cowell returned to Britain and began training at Newmarket and gained his first victory in January 1998 when Mary Cornwallis won at Lingfield Park.[4] In recent years Cowell has become renowned for his ability to take handicappers like Prohibit from other trainers and improving them to gain Black Type success.