[24] Jennifer Brady 4-6,3-6 Naomi Osaka [3] 2021-02-20 08:30
Stadium: Rod Laver Arena Round: 29 Ground: Hardcourt outdoor
Head to Head
| US Open Women | 2020/09/10 23:00 | Jennifer Brady v Naomi Osaka | 6-7,6-3,3-6 |
| WTA Charleston | 2018/04/02 17:30 | Jennifer Brady v Naomi Osaka | 4-6,4-6 |
Home History
| 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 |
| WTA Grampians Trophy | 2021/02/06 03:20 | Jennifer Brady v Barbora Krejcikova | 7-6,6-4 |
Away History
| Australian Open Women | 2021/02/18 03:00 | Naomi Osaka v Serena Williams | 6-3,6-4 |
| Australian Open Women | 2021/02/16 01:30 | Su-Wei Hsieh v Naomi Osaka | 2-6,2-6 |
| Australian Open Women | 2021/02/14 00:00 | Garbine Muguruza v Naomi Osaka | 6-4,4-6,5-7 |
| Australian Open Women | 2021/02/12 04:05 | Ons Jabeur v Naomi Osaka | 3-6,2-6 |
| Australian Open Women | 2021/02/10 08:00 | Caroline Garcia v Naomi Osaka | 2-6,3-6 |
| Australian Open Women | 2021/02/08 00:00 | Anastasia Pavlyuchenkova v Naomi Osaka | 1-6,2-6 |
| WTA Gippsland Trophy | 2021/02/05 07:45 | Irina-Camelia Begu v Naomi Osaka | 5-7,1-6 |
| WTA Gippsland Trophy | 2021/02/03 00:00 | Katie Boulter v Naomi Osaka | 6-3,3-6,1-6 |