[65] Sloane Stephens 6-4,2-6,5-7 Madison Keys [23] 2021-05-11 08:00
Stadium: Pietrangeli Round: 24 Ground: Clay
Head to Head
| WTA Charleston | 2021/04/07 23:15 | Sloane Stephens v Madison Keys | 6-4,6-4 |
| WTA Charleston | 2019/04/05 20:30 | Sloane Stephens v Madison Keys | 6-7,6-4,2-6 |
| French Open Women | 2018/06/07 14:50 | Madison Keys v Sloane Stephens | 4-6,4-6 |
| US Open Women | 2017/09/09 20:00 | Madison Keys v Sloane Stephens | 3-6,0-6 |
Home History
| WTA Rome | 2021/05/09 12:25 | Sloane Stephens v Tamara Zidansek | 4-6,5-7 |
| WTA Rome | 2021/05/08 17:20 | Sloane Stephens v Aliona Bolsova Zadoinov | 6-3,6-4 |
| WTA Madrid | 2021/05/01 12:55 | Sloane Stephens v Ons Jabeur | 6-4,1-6,3-6 |
| WTA Madrid | 2021/04/29 13:30 | Danka Kovinic v Sloane Stephens | 4-6,1-6 |
| WTA Charleston | 2021/04/09 23:20 | Veronika Kudermetova v Sloane Stephens | 6-3,6-4 |
| WTA Charleston | 2021/04/08 19:55 | Ajla Tomljanovic v Sloane Stephens | 3-6,4-6 |
| WTA Charleston | 2021/04/07 23:15 | Sloane Stephens v Madison Keys | 6-4,6-4 |
| WTA Charleston | 2021/04/06 15:55 | Sloane Stephens v Xinyu Wang | 6-2,6-4 |
Away History
| WTA Madrid | 2021/04/30 12:50 | Anastasia Pavlyuchenkova v Madison Keys | 7-5,6-2 |
| WTA Charleston | 2021/04/07 23:15 | Sloane Stephens v Madison Keys | 6-4,6-4 |
| WTA Miami | 2021/03/25 15:00 | Madison Keys v Ana Konjuh | 4-6,2-6 |
| WTA Dubai | 2021/03/09 08:00 | Madison Keys v Anastasia Potapova | 4-6,3-6 |
| WTA Dubai | 2021/03/08 08:00 | Madison Keys v En Shuo Liang | 6-1,6-1 |
| WTA Doha | 2021/03/03 14:15 | Maria Sakkari v Madison Keys | 6-2,6-2 |
| WTA Doha | 2021/03/02 15:00 | Madison Keys v Belinda Bencic | 6-4,6-1 |
| French Open Women | 2020/09/28 15:00 | Shuai Zhang v Madison Keys | 6-3,7-6 |