[66] Jennifer Brady 2-6,6-4,6-4 Madison Keys [15] 2019-09-22 14:30
Stadium: Lotus Round: 25 Ground: Hardcourt outdoor
Home History
| WTA Wuhan | 2019/09/22 05:45 | Jennifer Brady v Bernarda Pera | 4-6,6-3,4-6 |
| WTA Wuhan | 2019/09/21 03:00 | Jennifer Brady v Ellen Perez | 7-5,6-3 |
| WTA Wuhan | 2019/09/20 04:30 | Jennifer Brady v Yue Yuan | 6-4,6-3 |
| WTA New Haven | 2019/09/06 14:00 | Anna Blinkova v Jennifer Brady | 6-2,6-1 |
| WTA New Haven | 2019/09/05 14:00 | Nicole Gibbs v Jennifer Brady | 4-6,3-6 |
| WTA New Haven | 2019/09/04 14:00 | Quinn Gleason v Jennifer Brady | 2-6,5-7 |
| US Open Women | 2019/08/26 18:00 | Aliaksandra Sasnovich v Jennifer Brady | 6-1,4-6,6-0 |
| WTA Cincinnati | 2019/08/14 18:15 | Su-Wei Hsieh v Jennifer Brady | 7-6,6-3 |
Away History
| WTA Osaka | 2019/09/18 03:40 | Madison Keys v Zarina Diyas | 5-7,6-0,6-4 |
| WTA Osaka | 2019/09/17 02:00 | Madison Keys v Daria Kasatkina | 6-3,6-4 |
| US Open Women | 2019/09/01 23:00 | Elina Svitolina v Madison Keys | 7-5,6-4 |
| US Open Women | 2019/08/30 23:00 | Sofia Kenin v Madison Keys | 3-6,5-7 |
| US Open Women | 2019/08/28 20:25 | Lin Zhu v Madison Keys | 4-6,1-6 |
| US Open Women | 2019/08/27 02:20 | Misaki Doi v Madison Keys | 5-7,0-6 |
| WTA Cincinnati | 2019/08/18 18:00 | Svetlana Kuznetsova v Madison Keys | 5-7,6-7 |
| WTA Cincinnati | 2019/08/17 19:00 | Madison Keys v Sofia Kenin | 7-5,6-4 |