[13] Sofia Kenin 6-7,5-7 Madison Keys [51] 2021-10-07 15:20
Stadium: John Cain Arena Round: 23 Ground: Hardcourt outdoor
Head to Head
| US Invitational Women | 2020/06/27 20:00 | Sofia Kenin v Madison Keys | 3-6,7-5,2-10 |
| US Open Women | 2019/08/30 23:00 | Sofia Kenin v Madison Keys | 3-6,5-7 |
| WTA Cincinnati | 2019/08/17 19:00 | Madison Keys v Sofia Kenin | 7-5,6-4 |
| WTA Rome | 2019/05/16 10:50 | Madison Keys v Sofia Kenin | 7-6,3-6,4-6 |
Home History
| Wimbledon Women | 2021/06/30 17:40 | Madison Brengle v Sofia Kenin | 6-2,6-4 |
| Wimbledon Women | 2021/06/28 16:10 | Xinyu Wang v Sofia Kenin | 4-6,2-6 |
| French Open Women | 2021/06/07 13:55 | Sofia Kenin v Maria Sakkari | 1-6,3-6 |
| French Open Women | 2021/06/05 11:20 | Sofia Kenin v Jessica Pegula | 4-6,6-1,6-4 |
| French Open Women | 2021/06/03 09:00 | Sofia Kenin v Hailey Baptiste | 7-5,6-3 |
| French Open Women | 2021/05/31 14:25 | Sofia Kenin v Jelena Ostapenko | 6-4,4-6,6-3 |
| WTA Rome | 2021/05/12 13:40 | Sofia Kenin v Barbora Krejcikova | 1-6,4-6 |
| WTA Stuttgart | 2021/04/21 15:00 | Anett Kontaveit v Sofia Kenin | 7-5,6-4 |
Away History
| WTA Indian Wells | 2021/10/07 01:05 | Kaia Kanepi v Madison Keys | 0-6,5-7 |
| 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 |
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