[14] Madison Keys 7-6,3-6,4-6 Sofia Kenin [37] 2019-05-16 10:50
Stadium: Court 2 Round: 25 Ground: Clay
Home History
| WTA Rome | 2019/05/13 16:00 | Madison Keys v Polona Hercog | 6-4,7-6 |
| WTA Madrid | 2019/05/05 10:50 | Madison Keys v Sorana Cirstea | 6-3,4-6,1-6 |
| 2019 Fed Cup | 2019/04/20 19:30 | Madison Keys v Viktorija Golubic | 2-6,3-6 |
| WTA Charleston | 2019/04/07 17:00 | Madison Keys v Caroline Wozniacki | 7-6,6-3 |
| WTA Charleston | 2019/04/06 18:40 | Madison Keys v Monica Puig | 6-4,6-0 |
| WTA Charleston | 2019/04/05 20:30 | Sloane Stephens v Madison Keys | 6-7,6-4,2-6 |
| WTA Charleston | 2019/04/04 21:50 | Jelena Ostapenko v Madison Keys | 5-7,2-6 |
| WTA Charleston | 2019/04/03 23:00 | Tatjana Maria v Madison Keys | 6-7,6-4,4-6 |
Away History
| WTA Rome | 2019/05/13 19:10 | Sofia Kenin v Jasmine Paolini | 6-1,6-2 |
| WTA Madrid | 2019/05/04 17:00 | Sofia Kenin v Petra Kvitova | 1-6,4-6 |
| 2019 Fed Cup | 2019/04/21 20:35 | Sofia Kenin v Timea Bacsinszky | 6-3,7-6 |
| WTA Charleston | 2019/04/03 15:00 | Monica Puig v Sofia Kenin | 6-4,6-4 |
| WTA Charleston | 2019/04/01 14:00 | Sabine Lisicki v Sofia Kenin | 5-7,4-6 |
| WTA Miami | 2019/03/22 17:30 | Sofia Kenin v Bianca Andreescu | 3-6,3-6 |
| WTA Indian Wells | 2019/03/09 04:15 | Elina Svitolina v Sofia Kenin | 3-6,7-6,6-4 |
| WTA Indian Wells | 2019/03/06 22:10 | Yafan Wang v Sofia Kenin | 6-1,5-7,4-6 |