Crabbe had started out as a High Jumper who could sprint. At Central Arizona College and more so at Mississippi State University, he established himself as one of the leading sprinters on the US Collegiate circuit. In 2002 he earned All-America Honours in the 100m and 200m as well as in the sprint relay. His best times of 10.25 and 20.30 seconds remain national records in the 100 and 200 metres. At the end of 2002, Crabbe won the country’s first Gold medal at a multi-sport games, capturing the 100m title at the Central American and Caribbean Games in El Salvador. Dion Crabbe represented the BVI at age 27 during the 2004 Athens Summer Games. He competed in Round One of the 200m completing the race in 20.85