 At age three, Prospective Dolly's best stakes results were second-place finishes in the Miss Woodford Handicap at Monmouth Park Racetrack in New Jersey and the Star Shoot Stakes at Woodbine.As a four-year-old in 1991, Prospective Dolly won the first of her three Whimsical and Seaway Stakes at Woodbine.The next year, the five-year-old won her second straight Seaway Stakes and ran second in the Whimsical Stakes then in 1993 reversed her position in the two.