[50] Jelena Ostapenko 2-6,1-6 Jennifer Brady [14] 2021-05-02 14:15
Stadium: Arantxa Sanchez Stadium Round: 25 Ground: Clay
Head to Head
| WTA Dubai | 2019/02/18 11:20 | Jennifer Brady v Jelena Ostapenko | 6-4,6-0 |
| WTA Stuttgart Qual | 2017/04/24 09:00 | Jelena Ostapenko v Jennifer Brady | 5-7,6-1,6-3 |
Home History
| WTA Madrid | 2021/04/30 14:30 | Polona Hercog v Jelena Ostapenko | 3-6,1-6 |
| WTA Stuttgart | 2021/04/22 09:30 | Jelena Ostapenko v Karolina Pliskova | 7-6,4-6,3-6 |
| WTA Stuttgart | 2021/04/21 11:25 | Jelena Ostapenko v Stefanie Voegele | 6-4,7-5 |
| Billie Jean King Cup | 2021/04/16 15:00 | Jelena Ostapenko v Ankita Raina | 6-2,5-7,7-5 |
| WTA Miami | 2021/03/27 15:00 | Ashleigh Barty v Jelena Ostapenko | 6-3,6-2 |
| WTA Miami | 2021/03/25 17:30 | Jelena Ostapenko v Kirsten Flipkens | 6-2,5-7,6-3 |
| WTA Miami | 2021/03/24 17:00 | Jelena Ostapenko v Xiyu Wang | 6-4,6-7,6-1 |
| WTA St. Petersburg | 2021/03/17 20:00 | Jelena Ostapenko v Jaqueline Adina Cristian | 3-6,6-7 |
Away History
| WTA Madrid | 2021/04/30 16:10 | Venus Williams v Jennifer Brady | 2-6,4-6 |
| WTA Stuttgart | 2021/04/20 17:25 | Jennifer Brady v Petra Kvitova | 4-6,3-6 |
| WTA Miami | 2021/03/26 23:00 | Jennifer Brady v Sara Sorribes Tormo | 6-3,4-6,1-6 |
| WTA Doha | 2021/03/01 11:30 | Jennifer Brady v Anett Kontaveit | 1-6,2-6 |
| Australian Open Women | 2021/02/20 08:30 | Jennifer Brady v Naomi Osaka | 4-6,3-6 |
| Australian Open Women | 2021/02/18 04:40 | Karolina Muchova v Jennifer Brady | 4-6,6-3,4-6 |
| Australian Open Women | 2021/02/17 02:20 | Jennifer Brady v Jessica Pegula | 4-6,6-2,6-1 |
| Australian Open Women | 2021/02/15 02:15 | Donna Vekic v Jennifer Brady | 1-6,5-7 |