[76] Jennifer Brady 6-4,5-7,6-7 Simona Halep [4] 2019-08-07 17:20
Stadium: Centre Court Round: 25 Ground: Hardcourt outdoor
Home History
| WTA Toronto | 2019/08/05 15:00 | Jennifer Brady v Kristina Mladenovic | 6-1,6-2 |
| WTA Toronto | 2019/08/04 14:00 | Monica Puig v Jennifer Brady | 3-6,2-6 |
| WTA Toronto | 2019/08/03 14:00 | Shuai Peng v Jennifer Brady | 5-7,5-7 |
| WTA Washington | 2019/07/29 23:10 | Jennifer Brady v Sofia Kenin | 2-6,4-6 |
| Wimbledon Women | 2019/07/01 11:20 | Petra Martic v Jennifer Brady | 3-6,6-3,6-4 |
| WTA Birmingham | 2019/06/20 10:30 | Jennifer Brady v Ashleigh Barty | 3-6,1-6 |
| WTA Birmingham | 2019/06/19 10:30 | Jennifer Brady v Lesia Tsurenko | 6-3,6-3 |
| WTA Nottingham | 2019/06/15 13:50 | Caroline Garcia v Jennifer Brady | 4-6,6-3,6-3 |
Away History
| Wimbledon Women | 2019/07/13 13:00 | Serena Williams v Simona Halep | 2-6,2-6 |
| Wimbledon Women | 2019/07/11 12:00 | Elina Svitolina v Simona Halep | 1-6,3-6 |
| Wimbledon Women | 2019/07/09 12:00 | Simona Halep v Shuai Zhang | 7-6,6-1 |
| Wimbledon Women | 2019/07/08 13:25 | Simona Halep v Cori Gauff | 6-3,6-3 |
| Wimbledon Women | 2019/07/05 14:50 | Simona Halep v Victoria Azarenka | 6-3,6-1 |
| Wimbledon Women | 2019/07/03 13:35 | Simona Halep v Mihaela Buzarnescu | 6-3,4-6,6-2 |
| Wimbledon Women | 2019/07/01 12:00 | Simona Halep v Aliaksandra Sasnovich | 6-4,7-5 |
| WTA Eastbourne | 2019/06/27 11:55 | Angelique Kerber v Simona Halep | 6-4,6-3 |