Although Shedaresthedevil has been put away for the year and will not be contesting next month's Breeders' Cup, both Monomoy Girl and Serengeti Empress will carry the torch for past Kentucky Oaks (G1) winners when they compete in the Breeders' Cup Distaff (G1) and Filly and Mare Sprint (G1), respectively, at Keeneland on Nov. 7.
As is the case with Kentucky Derby winners competing in the Breeders' Cup Classic (G1), Kentucky Oaks winners have had varying degrees of success translating their success at Churchill Downs in the spring to the Breeders' Cup in the fall.
She didn't have a Breeders' Cup to compete in the year she won the Oaks in 1983, but Princess Rooney was one of the stars of the inaugural Cup in 1984 when demolishing her foes in the Distaff (G1) by seven lengths while running 1 1/4 miles a full second faster than the boys did an hour later in the Classic (G1). Finishing sixth in that Distaff was that season's Oaks heroine Lucky Lucky Lucky.
Fran's Valentine earned notoriety in the inaugural Breeders' Cup at Hollywood Park after she was disqualified from first and placed 10th in the Juvenile Fillies (G1). She won the Kentucky Oaks the following spring, but Breeders' Cup success continued to elude her as she finished fifth and second in the 1985 and 1986 editions of the Distaff, respectively.
The Distaff also proved a hard nut to crack by subsequent Oaks winners, including Goodbye Halo (3rd, 1988), Open Mind (3rd, 1989), Lite Light (6th, 1992), Dispute (4th, 1993), Keeper Hill (3rd, 1998), Silverbulletday (6th, 1999), Flute (7th, 2001), and Farda Amiga (2nd, 2002). In a majority of cases, the reigning Oaks winner was turned back by an older and more capable champion mare.
The Breeders' Cup was two decades old before a reigning Kentucky Oaks winner tasted success at it. Ashado was the first to make history, winning the 2004 Distaff at Lone Star Park, though she wound up third behind two longshots in her title defense at Belmont Park the following year.
Another dry spell ensued when Lemons Forever (5th, 2006), Blind Luck (2nd, 2010), and Plum Pretty (5th, 2011) all fell short in the Distaff. Princess of Sylmar was most disappointing of all in 2013 when she finished last of six at Santa Anita, but Untapable righted the ship in 2014 by taking the Distaff as the 8-5 favorite.
Abel Tasman, the 2017 Kentucky Oaks winner, took a couple swings at the Distaff. Beaten only a half-length into second the year she won the Oaks, in 2018 she crossed the wire last of 11. In front that day was the amazing Monomoy Girl, who figures to be one of the heavier favorites at this year's Breeders' Cup.
After displaying distance limitations when third in the 2019 Distaff and elsewhere, last year's Oaks winner Serengeti Empress is instead pointing to the 7-furlong Filly and Mare Sprint, a race she stands a better shot at winning. If both she and Monomoy Girl were to come out on top, it would be a noteworthy footnote in the long 146-year history of Churchill Downs' signature event for 3-year-old fillies.