Born in Trinidad and Tobago, Cuffy moved to the Caymans at a young age, and attended John Gray High School in George Town. He then studied at King College (in Bristol, Tennessee) on an athletic scholarship, winning both the 100 and 200-metre events at the 2008 National Association of Intercollegiate Athletics National Track Championships.
He has since competed for the Caymans in a number of international events and meets, notably winning two gold medals (in the 100 and 200 metres) at the 2015 Island Games. In his youth, Cuffy also represented the national under-19 cricket team, including at the 2005 Interstate Commerce Commission Americas Under-19 Championship. His father, Theo Cuffy, played first-class cricket in Trinidad and Tobago, and came to the Cayman Islands to coach the sport.
