[41] Jennifer Brady 6-7,6-3,3-6 Naomi Osaka [9] 2020-06-01 07:00
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
| Matchplay 120 Women | 2020/05/29 16:00 | Laura Siegemund v Jennifer Brady | 5-7,0-6 |
| WTA Doha | 2020/02/25 18:15 | Ons Jabeur v Jennifer Brady | 6-4,6-3 |
| WTA Doha | 2020/02/24 16:40 | Jennifer Brady v Alison Riske-Amritraj | 7-6,1-6,7-6 |
| WTA Dubai | 2020/02/21 15:30 | Simona Halep v Jennifer Brady | 6-2,6-0 |
| WTA Dubai | 2020/02/20 11:55 | Jennifer Brady v Garbine Muguruza | 6-7,6-3,6-4 |
| WTA Dubai | 2020/02/19 10:00 | Jennifer Brady v Marketa Vondrousova | 4-6,6-4,6-1 |
| WTA Dubai | 2020/02/18 10:00 | Elina Svitolina v Jennifer Brady | 2-6,1-6 |
| WTA Dubai | 2020/02/17 08:35 | Su-Wei Hsieh v Jennifer Brady | 2-6,2-6 |
Away History
| 2020 Fed Cup | 2020/02/07 11:10 | Sara Sorribes Tormo v Naomi Osaka | 6-0,6-3 |
| Australian Open Women | 2020/01/24 08:00 | Naomi Osaka v Cori Gauff | 3-6,4-6 |
| Australian Open Women | 2020/01/22 00:00 | Naomi Osaka v Saisai Zheng | 6-2,6-4 |
| Australian Open Women | 2020/01/20 00:00 | Naomi Osaka v Marie Bouzkova | 6-2,6-4 |
| WTA Brisbane | 2020/01/11 06:35 | Naomi Osaka v Karolina Pliskova | 7-6,6-7,2-6 |
| WTA Brisbane | 2020/01/10 04:30 | Kiki Bertens v Naomi Osaka | 3-6,6-3,3-6 |
| WTA Brisbane | 2020/01/09 09:00 | Sofia Kenin v Naomi Osaka | 7-6,3-6,1-6 |
| WTA Brisbane | 2020/01/07 03:25 | Maria Sakkari v Naomi Osaka | 2-6,7-6,3-6 |