Countess Diana launched her career on June 6, 1997 with a victory at Pimlico Race Course. She was trained during most of her two-year-old season by the relatively unknown Pat Byrne but by year’s end her accomplishments and those of stable mate Favorite Trick gave Byrne national recognition. She entered the Juvenile Fillies at Hollywood Park with just one defeat in four previous starts and cruised to an 8 1/2 length victory as the betting favorite. Her outstanding season earned her year-end honors as Eclipse Award champion as North America’s best juvenile filly. Winless in 1998, she added two more victories before retiring following her four-year-old campaign. She was sold for $1.8-million at public auction in early 2000.