[76] Jessica Pegula 3-6,6-7 Naomi Osaka [4] 2019-09-29 04:30
Stadium: Diamond Round: 24 Ground: Hardcourt outdoor
Home History
| WTA Wuhan | 2019/09/22 03:00 | Jessica Pegula v Polona Hercog | 0-6,1-6 |
| WTA Seoul | 2019/09/16 05:05 | Ysaline Bonaventure v Jessica Pegula | 5-7,6-2,6-4 |
| US Open Women | 2019/08/27 15:00 | Alize Cornet v Jessica Pegula | 6-2,6-3 |
| WTA Cincinnati | 2019/08/14 01:25 | Zarina Diyas v Jessica Pegula | 7-5,6-4 |
| WTA Cincinnati | 2019/08/10 18:20 | Mihaela Buzarnescu v Jessica Pegula | 3-6,6-7 |
| WTA Washington | 2019/08/04 18:00 | Camila Giorgi v Jessica Pegula | 2-6,2-6 |
| WTA Washington | 2019/08/03 17:00 | Jessica Pegula v Anna Kalinskaya | 6-3,3-6,6-1 |
| WTA Washington | 2019/08/02 18:00 | Jessica Pegula v Lauren Davis | 6-2,7-6 |
Away History
| WTA Osaka | 2019/09/22 03:00 | Naomi Osaka v Anastasia Pavlyuchenkova | 6-2,6-3 |
| WTA Osaka | 2019/09/21 06:45 | Naomi Osaka v Elise Mertens | 6-4,6-1 |
| WTA Osaka | 2019/09/21 03:00 | Naomi Osaka v Yulia Putintseva | 6-4,6-4 |
| WTA Osaka | 2019/09/18 08:10 | Naomi Osaka v Viktoriya Tomova | 7-5,6-3 |
| US Open Women | 2019/09/02 16:00 | Naomi Osaka v Belinda Bencic | 5-7,4-6 |
| US Open Women | 2019/08/31 23:00 | Naomi Osaka v Cori Gauff | 6-3,6-0 |
| US Open Women | 2019/08/29 16:55 | Naomi Osaka v Magda Linette | 6-2,6-4 |
| US Open Women | 2019/08/27 16:00 | Naomi Osaka v Anna Blinkova | 6-4,6-7,6-2 |