[26] Serena Williams 2-6,4-6 Naomi Osaka [19] 2018-09-08 20:00
Stadium: Arthur Ashe Stadium Round: 29 Ground: Hardcourt outdoor
Home History
| US Open Women | 2018/09/06 23:10 | Serena Williams v Anastasija Sevastova | 6-3,6-0 |
| US Open Women | 2018/09/04 23:10 | Serena Williams v Karolina Pliskova | 6-4,6-3 |
| US Open Women | 2018/09/02 19:45 | Kaia Kanepi v Serena Williams | 0-6,6-4,3-6 |
| US Open Women | 2018/09/01 00:00 | Serena Williams v Venus Williams | 6-1,6-2 |
| US Open Women | 2018/08/29 23:05 | Serena Williams v Carina Witthoeft | 6-2,6-2 |
| US Open Women | 2018/08/28 00:00 | Serena Williams v Magda Linette | 6-4,6-0 |
| WTA Cincinnati | 2018/08/15 00:30 | Petra Kvitova v Serena Williams | 6-3,2-6,6-3 |
| WTA Cincinnati | 2018/08/13 23:00 | Daria Saville v Serena Williams | 1-6,2-6 |
Away History
| US Open Women | 2018/09/07 00:35 | Madison Keys v Naomi Osaka | 2-6,4-6 |
| US Open Women | 2018/09/05 16:00 | Naomi Osaka v Lesia Tsurenko | 6-1,6-1 |
| US Open Women | 2018/09/03 17:40 | Aryna Sabalenka v Naomi Osaka | 3-6,6-2,4-6 |
| US Open Women | 2018/09/01 19:40 | Naomi Osaka v Aliaksandra Sasnovich | 6-0,6-0 |
| US Open Women | 2018/08/30 15:00 | Naomi Osaka v Julia Glushko | 6-2,6-0 |
| US Open Women | 2018/08/28 15:00 | Naomi Osaka v Laura Siegemund | 6-3,6-2 |
| WTA Cincinnati | 2018/08/14 15:00 | Naomi Osaka v Maria Sakkari | 3-6,6-7 |
| WTA Montreal | 2018/08/07 16:30 | Naomi Osaka v Carla Suarez Navarro | 6-7,2-6 |