[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 |