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 |
Home History
| French Open Women | 2020/09/28 13:05 | Kristie Ahn v Serena Williams | 6-7,0-6 |
| US Open Women | 2020/09/11 01:30 | Serena Williams v Victoria Azarenka | 6-1,3-6,3-6 |
| US Open Women | 2020/09/09 16:00 | Tsvetana Pironkova v Serena Williams | 6-4,3-6,2-6 |
| US Open Women | 2020/09/07 16:00 | Maria Sakkari v Serena Williams | 3-6,7-6,3-6 |
| US Open Women | 2020/09/05 18:10 | Sloane Stephens v Serena Williams | 6-2,2-6,2-6 |
| US Open Women | 2020/09/03 23:00 | Margarita Betova v Serena Williams | 2-6,4-6 |
| US Open Women | 2020/09/01 21:05 | Kristie Ahn v Serena Williams | 5-7,3-6 |
| WTA New York | 2020/08/26 00:40 | Maria Sakkari v Serena Williams | 5-7,7-6,6-1 |
Away History
| US Open Women | 2020/09/12 20:00 | Naomi Osaka v Victoria Azarenka | 1-6,6-3,6-3 |
| US Open Women | 2020/09/10 23:00 | Jennifer Brady v Naomi Osaka | 6-7,6-3,3-6 |
| US Open Women | 2020/09/08 23:00 | Naomi Osaka v Shelby Rogers | 6-3,6-4 |
| US Open Women | 2020/09/07 02:55 | Naomi Osaka v Anett Kontaveit | 6-3,6-4 |
| US Open Women | 2020/09/04 16:00 | Naomi Osaka v Marta Kostyuk | 6-3,6-7,6-2 |
| US Open Women | 2020/09/02 23:00 | Naomi Osaka v Camila Giorgi | 6-1,6-2 |
| US Open Women | 2020/09/01 01:35 | Naomi Osaka v Misaki Doi | 6-2,5-7,6-2 |
| WTA New York | 2020/08/28 15:00 | Elise Mertens v Naomi Osaka | 2-6,6-7 |