Her buyer, prominent Wall Street investor Carl Icahn, handed her over to trainer LeRoy Jolley for race conditioning.
Ridden by José A. Santos, Meadow Star was the overwhelming betting favorite for the 1990 Breeders' Cup Juvenile Fillies.
[3] Meadow Star's undefeated 1990 season made her the unanimous winner of the Eclipse Award for American Champion Two-Year-Old Filly.
After the two ran head-to-head from the turn at the top of the homestretch, Meadow Star won by a "lip" in a photo finish that took the officials six minutes to adjudicate.
After her loss in the Coaching Club American Oaks, Meadow Star was rested until early September, but in her return finished fourth in the one mile Maskette Stakes.
She did not race again until April 24, 1992, and after a season that saw her go winless in five starts with two third-place finishes her best showings, she was retired to broodmare service at Trackside Farm near Versailles, Kentucky.