In 1987, Trainer Tony Barnard was given charge of and broke Unbridled, at Tartan Farms, in Ocala, Florida. In 1989, at age two, Unbridled won the What A Pleasure Stakes and placed in all six of his starts. At age three, ridden by jockey Pat Day, he won the Grade I Florida Derby by four lengths, then finished second behind Summer Squall in the Blue Grass Stakes. He then won America's most prestigious race, the Kentucky Derby, by 3½ lengths with jockey Craig Perret, while Summer Squall finishing second. He finished second in the Preakness Stakes to Summer Squall, and finished fourth without Lasix in the Belmont Stakes to the Irish colt Go And Go. In the fall, ridden by Day, Unbridled won the 1¼ mile Breeders' Cup Classic at Belmont Park in 2:02.20 minutes. His performances for the year earned him the prestigious Eclipse Award as champion three-year-old male of 1990.