[100] Kaia Kanepi 2-6,3-6 Jennifer Brady [55] 2019-12-17 15:15
Stadium: Centre Round: 25 Ground: Hardcourt indoor
Home History
| ITF W15 Milovice | 2019/12/01 08:55 | Kaia Kanepi v Anastasia Kulikova | 6-4,6-3 |
| ITF W15 Milovice | 2019/11/30 10:30 | Kaia Kanepi v Linda Noskova | 6-2,6-2 |
| ITF W15 Milovice | 2019/11/29 10:45 | Kaia Kanepi v Caijsa W Hennemann | 6-2,6-1 |
| ITF W15 Milovice | 2019/11/28 13:00 | Kaia Kanepi v Miriam Kolodziejova | 6-2,7-5 |
| ITF W15 Milovice | 2019/11/27 12:30 | Kaia Kanepi v Darja Vidmanova | 6-2,6-4 |
| WTA Moscow | 2019/10/17 08:00 | Kaia Kanepi v Kiki Bertens | 6-4,3-6,5-7 |
| WTA Moscow | 2019/10/15 08:00 | Timea Babos v Kaia Kanepi | 1-6,3-6 |
| WTA Moscow | 2019/10/14 08:00 | Kaia Kanepi v Tereza Martincova | 6-2,6-3 |
Away History
| WTA Tianjin | 2019/10/08 05:30 | Ons Jabeur v Jennifer Brady | 6-4,6-2 |
| WTA Beijing | 2019/10/03 11:30 | Bianca Andreescu v Jennifer Brady | 6-1,6-3 |
| WTA Beijing | 2019/10/02 04:30 | Jennifer Brady v Madison Keys | 2-6,6-4,6-4 |
| WTA Beijing | 2019/09/30 04:30 | Jennifer Brady v Amanda Anisimova | 6-7,7-6,6-3 |
| WTA Beijing | 2019/09/28 03:00 | Jennifer Brady v Kateryna Baindl | 6-2,4-6,6-4 |
| WTA Beijing | 2019/09/27 03:00 | Jennifer Brady v Shilin Xu | 6-0,6-3 |
| WTA Wuhan | 2019/09/22 05:45 | Jennifer Brady v Bernarda Pera | 4-6,6-3,4-6 |
| WTA Wuhan | 2019/09/21 03:00 | Jennifer Brady v Ellen Perez | 7-5,6-3 |