In the 1996 Olympics, after having defeated Roland Raforme (Seychelles) and Paul M'Bongo (Cameroon), Ross lost 14–8 in quarterfinals to Kazakhstan's eventual gold medalist Vassili Jirov. Ross entered the 2000 Olympics as a gold medal hopeful, however he was eliminated after a disappointing loss in his first fight with a knockout at the 2nd round by a Nigerian boxer Jegbefumere Albert
Ross turned pro after the 2000 Summer Olympics, however he announced his retirement in 2005 after compiling a record of 13–1, due to the inability to get quality fights. In 2007 he began a comeback and on March 19, 2007, he captured the Commonwealth Cruiserweight title by knocking out John Keeton in the second round.
The Contender
In 2008 Ross joined the cast of the boxing reality TV show The Contender filming in Singapore. He became a member of the gold team and on 14 January 2009 won his first round contest against Australian Lawrence Tauasa.[3] He fought American Felix Cora Jr. in the quarterfinals winning when the fight was stopped after 2:48 of the first round.[3] In the semifinals Troy faced Nigerian Akinyemi Laleye, the fight was scored 50–45 by all three judges in Troy's favor. Troy fought another Nigerian, Ehinomen Ehikhamenor, in the finals on February 25, 2009, at the MGM Grand at Foxwoods Casino in Connecticut. Ross defeated Ehikhamenor by fourth-round TKO to become the Contender champion.[4]