The stakes is named for Jessamine County, formed in 1799 and a center of agriculture and Thoroughbred farms. Located to the southeast of Lexington, its county seat is Nicholasville. Keeneland Sales became the sponsor in 2023. The Jessamine (G2) Presented by Keeneland Sales is a Breeders' Cup Challenge "Win and You're In" race for the 2026 Breeders' Cup Juvenile Fillies Turf.

2025 Replay

In 2025 Imaginationthelady captured the Jessamine (G2) for trainer Brendan Walsh, jockey Frankie Dettori and owner Mark Dobbin.