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The Jenny Wiley Stakes is an American Thoroughbred horse race held annually during the second week of April at Keeneland Race Course in Lexington, Kentucky. The Grade II turf event is for fillies and Mares, age four and older and is contested at a distance of one and one-sixteenth miles.
The Jenny Wiley Stakes is named for Jenny Wiley, a pregnant pioneer woman captured in Kentucky by Native Americans in 1789 and who escaped after almost a year in captivity. Inaugurated in 1989 as a Listed race, in 1995 the Jenny Wiley Stakes was elevated to Grade III status and to a Grade II event in 2006.
| Stakes Race | Grade | Purse |
|---|---|---|
| Transylvania Stakes | III | $100,000 |
| Ashland Stakes | I | $400,000 |
| Madison Stakes | I | $300,000 |
| Maker's Mark Mile Stakes | I | $300,000 |
| Shakertown Stakes | III | $100,000 |
| Jenny Wiley Stakes | II | $200,000 |
| Commonwealth Stakes | II | $175,000 |
| Blue Grass Stakes | I | $750,000 |
| Beaumont Stakes | II | $150,000 |
| Appalachian Stakes | III | $100,000 |
| Doubledogdare Stakes | III | $100,000 |
| Ben Ali Stakes | III | $150,000 |
| Lexington Stakes | III | $200,000 |
| Bewitch Stakes | III | $150,000 |
| Elkhorn Stakes | II | $150,000 |
| Phoenix Stakes | III | $175,000 |
| Darley Alcibiades Stakes | I | $400,000 |
| Woodford Stakes | III | $100,000 |
| Thoroughbred Club of America Stakes | II | $200,000 |
| First Lady Stakes | I | $350,000 |
| Shadwell Turf Mile Stakes | I | $600,000 |
| Dixiana Breeders' Futurity Stakes | I | $400,000 |
| Bourbon Stakes | III | $100,000 |
| Juddmonte Spinster Stakes | I | $500,000 |
| Jessamine Stakes | III | $150,000 |
| Queen Elizabeth II Challenge Cup Stakes | I | $400,000 |
| Sycamore Stakes | III | $100,000 |
| Valley View Stakes | III | $150,000 |
| Raven Run Stakes | II | $250,000 |
| Fayette Stakes | II | $150,000 |
