[48] Jennifer Brady 6-2,7-6 Sloane Stephens [37] 2020-06-28 00:10
Round: 1
Home History
| US Invitational Women | 2020/06/25 17:00 | Jennifer Brady v Victoria Azarenka | 6-3,6-2 |
| Matchplay 120 Women | 2020/06/08 18:00 | Jennifer Brady v Jamie Loeb | 5-7,7-5,3-6 |
| Matchplay 120 Women | 2020/06/03 14:00 | Jamie Loeb v Jennifer Brady | 2-6,1-6 |
| 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 |
Away History
| US Invitational Women | 2020/06/27 01:45 | Eugenie Bouchard v Sloane Stephens | 3-6,6-7 |
| WTA Monterrey | 2020/03/05 01:50 | Leylah Annie Fernandez v Sloane Stephens | 6-7,6-3,6-3 |
| WTA Monterrey | 2020/03/03 03:45 | Emma Navarro v Sloane Stephens | 4-6,7-5,1-6 |
| WTA Acapulco | 2020/02/26 01:20 | Sloane Stephens v Renata Zarazua | 4-6,2-6 |
| Australian Open Women | 2020/01/20 10:05 | Sloane Stephens v Shuai Zhang | 6-2,5-7,2-6 |
| WTA Adelaide | 2020/01/14 00:30 | Arina Rodionova v Sloane Stephens | 6-2,6-2 |
| WTA Brisbane | 2020/01/07 01:00 | Sloane Stephens v Ludmilla Samsonova | 4-6,6-2,3-6 |
| WTA Beijing | 2019/10/01 09:05 | Saisai Zheng v Sloane Stephens | 6-3,6-1 |