Romans' life has revolved around racing. His father, Jerry, was a trainer based at Churchill Downs and Dale spent his youth in the barn area playing, working and absorbing the business. His racing education included a four-month stint with Hall of Fame trainer Woody Stephens. Romans took out his first training license at the age of 18 and won his first race in 1987 with a horse he bought for $1,500. His career moved to a new level in 2004 when he trained Kitten's Joy, winner of the Secretariat Stakes and the Joe Hirsch Turf Classic, who was voted the Eclipse Award as outstanding male turf horse. Roses in May was the runner-up to Ghostzapper in the 2004 Breeders' Cup Classic and returned in 2005 to win the Donn Handicap and the Dubai World Cup. Romans won his first Breeders' Cup race with Tapitsfly in the 2009 Juvenile Fillies Turf. In a Triple Crown training trifecta, Paddy O'Prado was third in the 2010 Kentucky Derby and stablemate First Dude was second in the Preakness and third in the Belmont Stakes. Romans won his first Triple Crown race in May 2011 with Shackleford in the Preakness and in November saddled long shot Court Vision for his stunning victory in the Breeders' Cup Mile.