[41] Jennifer Brady 6-7,6-3,3-6 Naomi Osaka [9] 2020-09-10 23:00
Stadium: Arthur Ashe Stadium Round: 28 Ground: Hardcourt outdoor
Head to Head
| WTA Charleston | 2018/04/02 17:30 | Jennifer Brady v Naomi Osaka | 4-6,4-6 |
Home History
| US Open Women | 2020/09/08 16:00 | Jennifer Brady v Yulia Putintseva | 6-3,6-2 |
| US Open Women | 2020/09/06 15:00 | Jennifer Brady v Angelique Kerber | 6-1,6-4 |
| US Open Women | 2020/09/04 17:20 | Caroline Garcia v Jennifer Brady | 3-6,3-6 |
| US Open Women | 2020/09/02 16:55 | Catherine Bellis v Jennifer Brady | 1-6,2-6 |
| US Open Women | 2020/09/01 01:20 | Anna Blinkova v Jennifer Brady | 3-6,2-6 |
| WTA New York | 2020/08/23 17:10 | Jennifer Brady v Jessica Pegula | 6-7,4-6 |
| WTA Lexington | 2020/08/16 15:00 | Jil Teichmann v Jennifer Brady | 3-6,4-6 |
| WTA Lexington | 2020/08/15 16:30 | Jennifer Brady v Cori Gauff | 6-2,6-4 |
Away History
| US Open Women | 2020/09/08 23:00 | Naomi Osaka v Shelby Rogers | 6-3,6-4 |
| US Open Women | 2020/09/07 02:55 | Naomi Osaka v Anett Kontaveit | 6-3,6-4 |
| US Open Women | 2020/09/04 16:00 | Naomi Osaka v Marta Kostyuk | 6-3,6-7,6-2 |
| US Open Women | 2020/09/02 23:00 | Naomi Osaka v Camila Giorgi | 6-1,6-2 |
| US Open Women | 2020/09/01 01:35 | Naomi Osaka v Misaki Doi | 6-2,5-7,6-2 |
| WTA New York | 2020/08/28 15:00 | Elise Mertens v Naomi Osaka | 2-6,6-7 |
| WTA New York | 2020/08/26 17:00 | Naomi Osaka v Anett Kontaveit | 4-6,6-2,7-5 |
| WTA New York | 2020/08/25 19:05 | Naomi Osaka v Dayana Yastremska | 6-3,6-1 |