[10] Serena Williams 6-3,6-4 Naomi Osaka [2] 2019-08-09 23:00
Stadium: Centre Court Round: 27 Ground: Hardcourt outdoor
Head to Head
| US Open Women | 2018/09/08 20:00 | Serena Williams v Naomi Osaka | 2-6,4-6 |
| WTA Miami | 2018/03/21 20:35 | Serena Williams v Naomi Osaka | 3-6,2-6 |
Home History
| WTA Toronto | 2019/08/08 23:00 | Serena Williams v Ekaterina Alexandrova | 7-5,6-4 |
| WTA Toronto | 2019/08/07 23:05 | Serena Williams v Elise Mertens | 6-3,6-3 |
| Wimbledon Women | 2019/07/13 13:00 | Serena Williams v Simona Halep | 2-6,2-6 |
| Wimbledon Women | 2019/07/11 13:30 | Serena Williams v Barbora Strycova | 6-1,6-2 |
| Wimbledon Women | 2019/07/09 12:00 | Alison Riske-Amritraj v Serena Williams | 4-6,6-4,3-6 |
| Wimbledon Women | 2019/07/08 12:00 | Serena Williams v Carla Suarez Navarro | 6-2,6-2 |
| Wimbledon Women | 2019/07/06 12:00 | Serena Williams v Julia Goerges | 6-3,6-4 |
| Wimbledon Women | 2019/07/04 15:40 | Serena Williams v Kaja Juvan | 2-6,6-2,6-4 |
Away History
| WTA Toronto | 2019/08/09 00:50 | Iga Swiatek v Naomi Osaka | 6-7,4-6 |
| Wimbledon Women | 2019/07/01 14:20 | Yulia Putintseva v Naomi Osaka | 7-6,6-2 |
| WTA Birmingham | 2019/06/20 13:20 | Naomi Osaka v Yulia Putintseva | 2-6,3-6 |
| WTA Birmingham | 2019/06/18 12:35 | Naomi Osaka v Maria Sakkari | 6-1,4-6,6-3 |
| French Open Women | 2019/06/01 12:25 | Naomi Osaka v Katerina Siniakova | 4-6,2-6 |
| French Open Women | 2019/05/30 09:00 | Naomi Osaka v Victoria Azarenka | 4-6,7-5,6-3 |
| French Open Women | 2019/05/28 13:30 | Naomi Osaka v Anna Karolina Schmiedlova | 0-6,7-6,6-1 |
| WTA Rome | 2019/05/16 15:45 | Naomi Osaka v Mihaela Buzarnescu | 6-3,6-3 |