He released his first EP, "Dream Out Loud", and was nominated for his first Golden Guitar for Best Male Vocalist in 1994. He has won many awards, the 1995 ARIA Award for 'Best Country Record', 1996 Country Music Awards in Tamworth, Troy won the 'Best Male Vocal' Award, 2000 CMAA Awards Best Male Vocal and Song Of The Year for 'They Don't Make 'Em Like That Anymore' and almost a decade's worth of Deadly Awards. He won the ARIA Music Award for best country album in 2006.