[74] Kaia Kanepi 1-6,6-3,1-6 Madison Keys [20] 2023-05-29 09:00
Stadium: Court 14 Round: 23 Ground: Clay
Head to Head
| WTA Indian Wells | 2021/10/07 01:05 | Kaia Kanepi v Madison Keys | 0-6,5-7 |
| US Open - Kvinner | 2017/09/06 23:00 | Madison Keys v Kaia Kanepi | 6-3,6-3 |
Home History
| WTA Strasbourg | 2023/05/23 11:30 | Clara Burel v Kaia Kanepi | 7-5,7-6 |
| WTA Strasbourg | 2023/05/21 10:00 | Xinyu Wang v Kaia Kanepi | 3-6,2-6 |
| WTA Roma | 2023/05/09 12:00 | Kaia Kanepi v Marketa Vondrousova | 0-6,6-4,2-6 |
| ITF W100 Wiesbaden | 2023/05/04 09:00 | Kaia Kanepi v Dalila Jakupovic | 3-6,2-6 |
| ITF W100 Wiesbaden | 2023/05/02 13:35 | Kaia Kanepi v Joelle Lilly Sophie Steur | 6-0,6-1 |
| WTA Madrid | 2023/04/26 13:00 | Kaia Kanepi v Irene Burillo Escorihuela | 7-6,2-6,4-6 |
| WTA Charleston | 2023/04/03 14:00 | Kaia Kanepi v Madison Brengle | 3-6,4-6 |
| WTA Miami | 2023/03/21 18:40 | Camila Giorgi v Kaia Kanepi | 7-6,6-7,7-6 |
Away History
| WTA Roma | 2023/05/15 09:00 | Madison Keys v Anhelina Kalinina | 6-2,2-6,4-6 |
| WTA Roma | 2023/05/11 12:45 | Magdalena Frech v Madison Keys | 3-6,2-6 |
| WTA Charleston | 2023/04/07 18:30 | Madison Keys v Daria Kasatkina | 7-6,4-6,2-6 |
| WTA Charleston | 2023/04/07 00:10 | Magda Linette v Madison Keys | 2-6,6-3,1-6 |
| WTA Charleston | 2023/04/05 17:05 | Hailey Baptiste v Madison Keys | 1-6,2-6 |
| WTA Charleston | 2023/04/04 16:50 | Emma Navarro v Madison Keys | 4-6,3-6 |
| WTA Miami | 2023/03/26 21:15 | Barbora Krejcikova v Madison Keys | 7-6,6-3 |
| WTA Miami | 2023/03/24 18:35 | Robin Montgomery v Madison Keys | 4-6,4-6 |