Round: 27 Ground: Hardcourt outdoor
| 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 18:25 | Maria Sakkari v Ying-Ying Duan | 4-6,6-4,3-6 |
| US Open 2016 Women | 2016/08/26 16:35 | Ying-Ying Duan v Rebecca Peterson | 7-5,6-3 |
| US Open 2016 Women | 2016/08/25 19:10 | Ying-Ying Duan v Miyu Kato | 7-5,6-4 |
| US Open 2016 Women | 2016/08/24 15:00 | Ying-Ying Duan v Ons Jabeur | 5-7,6-1,6-4 |
| Wimbledon Women | 2016/06/30 14:55 | Ying-Ying Duan v Roberta Vinci | 3-6,5-7 |
| Wimbledon Women | 2016/06/28 10:30 | Kristyna Pliskova v Ying-Ying Duan | 3-6,6-3,5-7 |
| Wimbledon Women Qual | 2016/06/24 14:20 | Aleksandra Krunic v Ying-Ying Duan | 6-2,6-4 |
| US Open 2016 Women | 2016/09/06 01:40 | Agnieszka Radwanska v Ana Konjuh | 4-6,4-6 |
| US Open 2016 Women | 2016/09/03 16:35 | Agnieszka Radwanska v Caroline Garcia | 6-2,6-3 |
| US Open 2016 Women | 2016/09/01 21:45 | Agnieszka Radwanska v Naomi Broady | 7-6,6-3 |
| US Open 2016 Women | 2016/08/30 23:20 | Agnieszka Radwanska v Jessica Pegula | 6-1,6-1 |
| WTA Montreal | 2016/07/28 18:30 | Agnieszka Radwanska v Anastasia Pavlyuchenkova | 4-6,7-6,1-6 |
| WTA Montreal | 2016/07/27 16:30 | Agnieszka Radwanska v Monica Niculescu | 6-1,7-5 |
| Wimbledon Women | 2016/07/04 10:30 | Agnieszka Radwanska v Dominika Cibulkova | 3-6,7-5,7-9 |
| Wimbledon Women | 2016/07/02 18:25 | Agnieszka Radwanska v Katerina Siniakova | 6-3,6-1 |