As a 2-year-old of 1999, Darling My Darling finished second in both the Frizette and Matron Stakes, both grade I, then won last year's Raven Run Stakes at Keeneland over Surfside. She is trained by John Ward for Debbie Oxley.
Darling My Darling, who had not started since finishing sixth in the Churchill Downs Distaff (gr. II) last November, returned victoriously to racing with a 1 1/4-length win in Gulfstream Park's eighth race Monday. As the 3-5 favorite, Darling My Darling and jockey Mike Smith broke last in the field of six, then stayed in fifth for the first half-mile of 6 1/2-furlong sprint race. At the stretch call, Penny Blues had the lead and Darling My Darling was still fourth. She made up ground fast and went on to win with a late drive over People's Princess. The winner paid $3.40.