[53] Katerina Siniakova 3-6,7-5,2-6 Anett Kontaveit [30] 2021-08-26 22:00
Stadium: Stadium Court Round: 27 Ground: Hardcourt outdoor
Head to Head
| WTA Wuhan | 2018/09/27 12:10 | Anett Kontaveit v Katerina Siniakova | 6-4,6-4 |
| US Open - Kobiety | 2018/08/28 23:50 | Anett Kontaveit v Katerina Siniakova | 7-6,3-6,5-7 |
| WTA Guangzhou | 2016/09/20 06:10 | Anett Kontaveit v Katerina Siniakova | 6-1,6-1 |
Home History
| WTA Cleveland | 2021/08/25 15:30 | Katerina Siniakova v Nagi Hanatani | 6-0,6-0 |
| WTA Cleveland | 2021/08/23 23:50 | Shelby Rogers v Katerina Siniakova | 5-7,1-6 |
| WTA Montreal | 2021/08/12 16:00 | Sara Sorribes Tormo v Katerina Siniakova | 6-7,6-0,6-3 |
| WTA Montreal | 2021/08/10 16:25 | Katerina Siniakova v Garbine Muguruza | 6-2,0-6,6-3 |
| WTA Montreal | 2021/08/09 15:00 | Jelena Ostapenko v Katerina Siniakova | 1-6,3-6 |
| WTA Praga | 2021/07/16 12:35 | Katerina Siniakova v Barbora Krejcikova | 3-6,0-6 |
| WTA Praga | 2021/07/14 15:00 | Katerina Siniakova v Tereza Smitkova | 2-6,7-6,6-3 |
| WTA Praga | 2021/07/13 13:00 | Katerina Siniakova v Jodie Anna Burrage | 6-0,6-4 |
Away History
| WTA Cleveland | 2021/08/25 20:30 | Caroline Garcia v Anett Kontaveit | 3-6,3-6 |
| WTA Cleveland | 2021/08/23 22:00 | Lauren Davis v Anett Kontaveit | 6-1,0-6,0-6 |
| WTA Cincinnati | 2021/08/18 00:25 | Ons Jabeur v Anett Kontaveit | 6-2,4-6,7-5 |
| WTA Montreal | 2021/08/10 15:00 | Anett Kontaveit v Jessica Pegula | 7-5,3-6,3-6 |
| Olimpiada 2020 - Kobiety | 2021/07/24 03:30 | Maria Sakkari v Anett Kontaveit | 7-5,6-2 |
| Wimbledon - Kobiety | 2021/06/30 13:45 | Marketa Vondrousova v Anett Kontaveit | 2-6,6-4,6-2 |
| WTA Eastbourne | 2021/06/26 11:30 | Anett Kontaveit v Jelena Ostapenko | 3-6,3-6 |
| WTA Eastbourne | 2021/06/24 10:00 | Anett Kontaveit v Viktorija Golubic | 2-6,7-6,7-5 |