[60] Kaia Kanepi 0-6,5-7 Madison Keys [50] 2021-10-07 01:05
Stadium: Stadium 1 Round: 23 Ground: Hardcourt outdoor
Head to Head
| US Open Women | 2017/09/06 23:00 | Madison Keys v Kaia Kanepi | 6-3,6-3 |
Home History
| WTA Chicago | 2021/09/28 14:00 | Jil Teichmann v Kaia Kanepi | 7-6,7-5 |
| ITF W25 Fort Worth | 2021/09/26 14:30 | Kaia Kanepi v Kayla Day | 6-2,6-1 |
| ITF W25 Fort Worth | 2021/09/25 14:30 | Kaia Kanepi v Alexandra Bozovic | 3-6,6-3,6-4 |
| ITF W25 Fort Worth | 2021/09/24 14:30 | Kaia Kanepi v Emma Navarro | 6-2,6-2 |
| ITF W25 Fort Worth | 2021/09/23 15:10 | Kaia Kanepi v Quinn Gleason | 6-3,6-2 |
| ITF W25 Fort Worth | 2021/09/21 18:10 | Kaia Kanepi v Sophie Chang | 6-1,5-7,6-1 |
| US Open Women | 2021/09/01 15:50 | Kaia Kanepi v Leylah Annie Fernandez | 5-7,5-7 |
| US Open Women | 2021/08/30 15:00 | Yulia Putintseva v Kaia Kanepi | 6-2,6-7,2-6 |
Away History
| US Open Women | 2021/08/30 16:00 | Madison Keys v Sloane Stephens | 3-6,6-1,6-7 |
| WTA Cincinnati | 2021/08/16 18:45 | Petra Kvitova v Madison Keys | 7-5,6-4 |
| WTA Montreal | 2021/08/10 01:30 | Rebecca Marino v Madison Keys | 6-3,6-3 |
| WTA San Jose | 2021/08/05 02:00 | Shuai Zhang v Madison Keys | 7-5,7-6 |
| Wimbledon Women | 2021/07/05 14:10 | Madison Keys v Viktorija Golubic | 6-7,3-6 |
| Wimbledon Women | 2021/07/02 17:10 | Elise Mertens v Madison Keys | 5-7,3-6 |
| Wimbledon Women | 2021/06/30 17:45 | Lauren Davis v Madison Keys | 1-6,4-6 |
| Wimbledon Women | 2021/06/28 14:30 | Katie Swan v Madison Keys | 3-6,4-6 |