[74] Jennifer Brady 2-6,6-7 Anett Kontaveit [27] 2018-04-05 10:15
Stadium: Court 14 Round: 24 Ground: Grass
Home History
| WTA Charleston | 2018/04/02 17:30 | Jennifer Brady v Naomi Osaka | 4-6,4-6 |
| WTA Miami | 2018/03/21 15:00 | Zarina Diyas v Jennifer Brady | 7-5,7-6 |
| WTA Indian Wells | 2018/03/11 01:35 | Caroline Garcia v Jennifer Brady | 6-4,6-4 |
| WTA Indian Wells | 2018/03/09 00:15 | Jennifer Brady v Mihaela Buzarnescu | 3-6,6-4,6-2 |
| WTA Indian Wells | 2018/02/27 21:45 | Sara Errani v Jennifer Brady | 6-2,6-2 |
| ITF Women Midland | 2018/02/03 23:00 | Jamie Loeb v Jennifer Brady | 7-5,4-6,6-4 |
| ITF Women Midland | 2018/02/02 15:00 | Bianca Andreescu v Jennifer Brady | 4-6,5-7 |
| ITF Women Midland | 2018/02/01 18:15 | Francoise Abanda v Jennifer Brady | 4-6,2-6 |
Away History
| WTA Miami | 2018/03/23 18:15 | Anett Kontaveit v Maria Sakkari | 4-6,1-6 |
| WTA Indian Wells | 2018/03/10 19:00 | Anett Kontaveit v Aliaksandra Sasnovich | 2-6,4-6 |
| WTA Dubai | 2018/02/21 10:00 | Anett Kontaveit v Naomi Osaka | 2-6,6-7 |
| WTA Dubai | 2018/02/20 11:30 | Anett Kontaveit v Samantha Stosur | 1-6,6-2,6-4 |
| WTA Doha | 2018/02/13 12:30 | Anett Kontaveit v Alize Cornet | 2-6,1-6 |
| 2018 Fed Cup | 2018/02/09 15:15 | Johanna Konta v Anett Kontaveit | 6-7,6-4,6-2 |
| Australian Open Women | 2018/01/21 00:00 | Anett Kontaveit v Carla Suarez Navarro | 6-4,4-6,6-8 |
| Australian Open Women | 2018/01/19 10:15 | Jelena Ostapenko v Anett Kontaveit | 3-6,6-1,3-6 |