| Age | Starts | 1st | 2nd | 3rd | Earnings | |
| 3 | 3 | 1 | 0 | 1 | $80,891 |
|
| 4 | 8 | 4 | 1 | 2 | $400,394 |
|
| 5 | 2 | 0 | 0 | 1 | $8,019 |
|
At 3: 1– Bouwerie S., 3– Cicada S. (G3)
At 4: 1– Barbara Fritchie Breeders' Cup H. (G2), Regret S., Interborough H., Schenectady H., 2– Vagrancy H. (G2), 3– Distaff Breeders' Cup H. (G2), Garland of Roses H.
At 5: 3– Interborough H.
Won Schenectady H. on Sept. 9 at Belmont
Oprah Winney continued her dominance at Belmont Park with an easy 3 1/4-length victory on September 9 in the Schenectady Handicap over four overmatched opponents. The victory was her third in five starts at Belmont to go along with a second and a third.
Trainer Richard Dutrow Jr. used the Schenectady as a "nice easy race" in anticipation of the inaugural Breeders' Cup Filly and Mare Sprint, recognizing the timing was ideal.
Oprah Winney was an easy winner in her previous start, the Regret Stakes on August 5 at Monmouth Park, site of this year's Breeders' Cup.
"She's been training like clockwork for three months now," Dutrow said prior to the Schenectady. "She's really stepped it up and everyone around the barn knows she's stepped it up."
Jockey Edgar Prado, who had ridden Oprah Winney in six previous races, missed the mount in the Schenectady, having suffered a broken ankle at the end of the Saratoga meeting, so Dutrow turned to Garrett Gomez for the race.
If Prado remains unavailable for the Breeders' Cup, Dutrow hopes to keep Gomez aboard, particularly since he gained experience with her in the Schenectady.
October 19 - Five furlongs handily in :59.45 at Aqueduct, track fast. Best of nine workouts at the distance.
October 13 - Six furlongs breezing in 1:13.39 at Aqueduct, track fast. Best of five workouts at the distance.
October 5 - Five furlongs handily in 1:00.37 at Aqueduct, track fast. Best of ten workouts at the distance.
September 29 - Five furlongs breezing in 1:02.16 at Aqueduct, track fast. Sixth best of 17 workouts at the distance.
September 23 - Four furlongs breezing in :47.21 at Aqueduct, track fast. Best of 16 workouts at the distance.