Sunday’s $500,000 Spinster S. (G1) at Keeneland holds the distinction of being the final “Win & You’re In” Challenge race offering a guaranteed berth into the Breeders’ Cup Distaff (G1) but is also significant for another reason as well.

The 1 1/8-mile contest features both Untapable and Lovely Maria, winners of the past two editions of the Kentucky Oaks (G1), and will be the first time since the 2006 Spinster that Oaks winners have faced off. In that edition, 2005 Oaks scorer Summerly finished seventh to 2006 Oaks victress Lemons Forever’s fifth-placing.

Untapable prevailed in the Kentucky Oaks during her 2014 championship season. The bay daughter of Tapit went 6-0-0 from seven starts last year, with her only loss coming as a fifth in the Haskell Invitational (G1). The Steven Asmussen trainee closed out her sophomore campaign with a nice win in the Breeders’ Cup Distaff to lock up the Eclipse Award as the year’s champion three-year-old filly.

Unfortunately, Untapable hasn’t been the same filly in five starts this year. She hasn’t done bad, but that above-average spark seems to be missing. Her only win came in the Apple Blossom H. (G1) in April, with a second in the Azeri S. (G2) preceding that one. She followed up with two more runner-up efforts in the Ogden Phipps S. (G1) and Shuvee H. (G3), and her most recent race produced a third in the Personal Ensign S. (G1) at Saratoga. John Velazquez has the call.

Lovely Maria isn’t exactly entering the race in stellar form either but does own a top-level win over the track thanks to her Ashland S. (G1) victory in April. The Larry Jones pupil then captured the Kentucky Oaks under the Twin Spires but has been unable to find the top three in two starts since.

After a brief freshening, Lovely Maria showed up in the July 11 Delaware Oaks (G3) and ended up fifth. That race was a prep for the Ashland S. (G1) at Saratoga but the Majesticperfection filly finished sixth-of-seven on that occasion. She’s entering the Spinster off that subpar run and keeps regular rider Kerwin Clark aboard.

While much of the attention will be focused on Untapable and Lovely Maria, there are seven other distaffers in the Spinster field. Two with a good shot are Got Lucky and Frivolous.

Got Lucky romped in both the Molly Pitcher S. (G3) and Lady’s Secret S. prior to her last race, which resulted in a rallying second in the Personal Ensign Invitational (G1) at Saratoga. Frivolous sandwiched a nice second in the Delaware H. (G1) between victory in the Fleur de Lis H. (G2) and an eight-length romp in the Locust Grove S. at Churchill Downs on September 12.

One race before the Spinster, an overflow field of 16 juvenile colts and geldings will get their shot at an assured spot in the Breeders’ Cup Juvenile Turf (G1) gate in the $250,000 Bourbon S. (G3).

The 1 1/16-mile turf contest boasts Sunday Silence S. winner Uncle Brennie, Tyro S. victor Expected Ruler, With Anticipation S. (G2) third Unbridled Daddy, Del Mar Juvenile Turf runner-up Hot Ore and an assortment of maiden winners.

Untapable photo courtesy of Oaklawn Park/Coady Photography
Lovely Maria photo courtesy of Churchill Downs/Reed Palmer Photography