[31] Jelena Ostapenko 5-7,2-6 Madison Keys [18] 2019-04-04 21:50
Stadium: Credit One Stadium Round: 26 Ground: Clay
Home History
| WTA Charleston | 2019/04/03 17:40 | Jelena Ostapenko v Shelby Rogers | 4-6,6-3,7-6 |
| WTA Charleston | 2019/04/01 15:45 | Jelena Ostapenko v Johanna Larsson | 6-1,6-4 |
| WTA Miami | 2019/03/22 16:35 | Marketa Vondrousova v Jelena Ostapenko | 7-5,6-1 |
| WTA Indian Wells | 2019/03/10 20:40 | Marketa Vondrousova v Jelena Ostapenko | 4-6,6-3,6-4 |
| WTA Indian Wells | 2019/03/08 21:05 | Shuai Zhang v Jelena Ostapenko | 2-6,1-6 |
| WTA Dubai | 2019/02/18 11:20 | Jennifer Brady v Jelena Ostapenko | 6-4,6-0 |
| WTA Doha | 2019/02/13 12:30 | Elina Svitolina v Jelena Ostapenko | 6-4,6-4 |
| WTA Doha | 2019/02/12 14:00 | Mihaela Buzarnescu v Jelena Ostapenko | 1-6,6-4,2-6 |
Away History
| WTA Charleston | 2019/04/03 23:00 | Tatjana Maria v Madison Keys | 6-7,6-4,4-6 |
| WTA Miami | 2019/03/21 23:30 | Samantha Stosur v Madison Keys | 6-4,4-6,6-4 |
| WTA Indian Wells | 2019/03/09 20:20 | Madison Keys v Mona Barthel | 6-3,1-6,5-7 |
| 2019 Fed Cup | 2019/02/10 18:00 | Madison Keys v Ashleigh Barty | 4-6,1-6 |
| 2019 Fed Cup | 2019/02/09 19:40 | Madison Keys v Kimberly Birrell | 6-2,6-2 |
| Australian Open Women | 2019/01/21 00:00 | Madison Keys v Elina Svitolina | 2-6,6-1,1-6 |
| Australian Open Women | 2019/01/19 04:45 | Elise Mertens v Madison Keys | 3-6,2-6 |
| Australian Open Women | 2019/01/17 02:00 | Anastasia Potapova v Madison Keys | 3-6,4-6 |