Twilight Gleaming made her debut at Keeneland Racecourse and finished a hard fought second. She sparkled in her next start, skipping away to break her maiden by 7 1/2 lengths at Belmont Park. Twilight Gleaming followed in the footsteps of fellow girls in gold Lady Aurelia and Campanelle and ventured overseas to Royal Ascot. She impressed in her first foreign outing, finishing second in the G2 Queen Mary Stakes. Twilight Gleaming then journeyed to France and conquered the Prix de la Vallee d’Auge by a half length. After a break from the races, Twilight Gleaming burst onto the world stage and beat the boys in the Breeders’ Cup Juvenile Turf Sprint. In her first race of 2022, Twilight Gleaming finished second in the Palisades Stakes at Keeneland. She quickly returned to her winning ways with a determined victory in the Mamzelle Stakes at Churchill Downs. She has since added the Daisycutter Stakes to her impressive resume. After a break from the races, Twilight Gleaming shined in her 2023 debut, winning the Giant’s Causeway Stakes at Keeneland in stakes record time. Twilight Gleaming was trained by Wesley Ward and joined Stonestreet Stables following her purchase from the Goffs Orby Yearling Sale.

Twilight Gleaming retired to the Stonestreet broodmare band with a record of 6 wins from 14 starts and earnings of $931,317. She welcomed her first foal for the 2025 season, a colt by Triple Crown winner, Justify.