Madison Keys 7-5,4-6,7-6 Naomi Osaka 2016-08-03 07:00
Stadium: Arthur Ashe Stadium Round: 25
Home History
| WTA Montreal | 2016/07/31 17:00 | Madison Keys v Simona Halep | 6-7,3-6 |
| WTA Montreal | 2016/07/30 22:00 | Kristina Kucova v Madison Keys | 2-6,1-6 |
| WTA Montreal | 2016/07/29 22:30 | Anastasia Pavlyuchenkova v Madison Keys | 6-7,6-1,0-6 |
| WTA Montreal | 2016/07/28 22:30 | Madison Keys v Venus Williams | 6-1,6-7,6-3 |
| WTA Montreal | 2016/07/27 21:15 | Madison Keys v Madison Brengle | 6-4,6-3 |
| WTA Montreal | 2016/07/26 18:45 | Madison Keys v Elena Vesnina | 6-4,6-0 |
| Wimbledon Women | 2016/07/04 12:00 | Simona Halep v Madison Keys | 6-7,6-4,6-3 |
| Wimbledon Women | 2016/07/02 16:15 | Alize Cornet v Madison Keys | 4-6,7-5,2-6 |
Away History
| WTA Montreal Qual | 2016/07/23 15:15 | Alla Kudryavtseva v Naomi Osaka | 3-6,7-6,6-4 |
| Challenger Kaohsiung | 2016/02/09 02:30 | Mandy Minella v Naomi Osaka | 6-2,7-6 |
| Wimbledon Women Qual | 2015/06/23 12:30 | Naomi Osaka v Sorana Cirstea | 6-2,1-6,4-6 |
| WTA Bogota Qual | 2015/04/11 17:00 | Naomi Osaka v Laura Pous Tio | 1-6,3-6 |