Head to Head
| WTA Toronto | 2019/08/09 23:00 | Serena Williams v Naomi Osaka | 6-3,6-4 |
| 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 |
| WTA Toronto | 2019/08/09 23:00 | Serena Williams v Naomi Osaka | 6-3,6-4 |
| 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 |