Naomi Osaka 6-0,6-2 Anett Kontaveit 2016-09-13 05:00
Ground: Hardcourt outdoor
Home History
| US Open 2016 Women | 2016/09/02 17:00 | Madison Keys v Naomi Osaka | 7-5,4-6,7-6 |
| US Open 2016 Women | 2016/08/31 19:45 | Ying-Ying Duan v Naomi Osaka | 4-6,6-7 |
| US Open 2016 Women | 2016/08/29 16:50 | Naomi Osaka v Coco Vandeweghe | 6-7,6-3,6-4 |
| 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 |
Away History
| US Open 2016 Women | 2016/08/30 17:55 | Anett Kontaveit v Elena Vesnina | 6-7,6-4,3-6 |
| Wimbledon Women | 2016/06/29 16:45 | Anett Kontaveit v Barbora Strycova | 6-4,4-6,4-6 |
| Billie Jean King Cup | 2016/02/05 14:50 | Cagla Buyukakcay v Anett Kontaveit | 6-7,4-6 |
| Billie Jean King Cup | 2016/02/04 14:55 | Anett Kontaveit v Julia Glushko | 3-6,3-6 |
| Billie Jean King Cup | 2016/02/03 15:25 | Ana Konjuh v Anett Kontaveit | 6-4,3-6,4-6 |
| Wimbledon Women | 2015/06/29 10:30 | Anett Kontaveit v Victoria Azarenka | 2-6,1-6 |
| Wimbledon Women Qual | 2014/06/18 12:20 | Anett Kontaveit v Sesil Karatantcheva | 6-2,2-6,6-2 |
| Wimbledon Women Qual | 2014/06/17 13:35 | Saisai Zheng v Anett Kontaveit | 2-6,1-6 |