[13] Jennifer Brady 1-6,2-6 Anett Kontaveit [24] 2021-03-01 11:30
Stadium: Centre Court Round: 25 Ground: Hardcourt outdoor
Head to Head
| Wimbledon Women | 2018/07/05 16:15 | Jennifer Brady v Anett Kontaveit | 2-6,6-7 |
Home History
| 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 |
| Australian Open Women | 2021/02/13 02:30 | Jennifer Brady v Kaja Juvan | 6-1,6-3 |
| Australian Open Women | 2021/02/11 04:15 | Jennifer Brady v Madison Brengle | 6-1,6-2 |
| Australian Open Women | 2021/02/09 02:15 | Jennifer Brady v Aliona Bolsova Zadoinov | 6-1,6-3 |
| WTA Grampians Trophy | 2021/02/07 02:20 | Jennifer Brady v Ann Li | 6-7,7-6,6-10 |
Away History
| Australian Open Women | 2021/02/13 08:00 | Anett Kontaveit v Shelby Rogers | 4-6,3-6 |
| Australian Open Women | 2021/02/11 03:30 | Anett Kontaveit v Heather Watson | 6-7,6-4,6-2 |
| Australian Open Women | 2021/02/09 06:10 | Anett Kontaveit v Aliaksandra Sasnovich | 7-5,6-2 |
| WTA Grampians Trophy | 2021/02/07 00:30 | Maria Sakkari v Anett Kontaveit | 6-2,3-6,9-11 |
| WTA Grampians Trophy | 2021/02/05 02:00 | Bethanie Mattek-Sands v Anett Kontaveit | 5-7,5-7 |
| WTA Grampians Trophy | 2021/02/03 01:35 | Christina McHale v Anett Kontaveit | 1-6,3-6 |
| WTA Abu Dhabi | 2021/01/06 08:05 | Veronika Kudermetova v Anett Kontaveit | 7-5,6-1 |
| WTA Ostrava | 2020/10/21 17:30 | Anett Kontaveit v Sara Sorribes Tormo | 1-6,4-6 |