Trained by Darwin Banach, Sky Conqueror was sent to the track at age three with his best Stakes race result a second in the Chief Bearhart Stakes at Woodbine Racetrack in Toronto and a third at Churchill Downs in November's Commonwealth Turf Stakes. Back on the track in April 2006, he had a fourth place finish at Keeneland before being sent north to race again at Woodbine. After another third-place finish, he won the Grade II King Edward Breeders' Cup Stakes and the Northern Dancer Breeders' Cup Turf. He won an allowance race tune-up for the prestigious $2 million Canadian International Stakes in which he ran third.
Sky Conqueror made his 2007 debut in April at Keeneland, finishing fifth in the Grade II Maker's Mark Mile Stakes. In May, he defeated Better Talk Now and the favored Einstein in winning the Grade I Turf Classic Stakes at Churchill Downs. Back at Woodbine, in July he won his second consecutive Northern Dancer Breeder's Cup Turf. In August he finished third in the Nijinsky Stakes.