Round: 25 Ground: Hardcourt outdoor
| ITF Damen - Las Vegas - Qualifikation | 2016/09/27 16:30 | Julia Elbaba v Chanel Simmonds | 6-2,4-6,6-3 |
| ITF Damen - Las Vegas - Qualifikation | 2016/09/26 16:30 | Ai Wen Zhu v Chanel Simmonds | 1-6,0-6 |
| ITF Damen - Las Vegas - Qualifikation | 2016/09/25 21:50 | Jessica Wacnik v Chanel Simmonds | 6-4,4-6,3-6 |
| ITF Damen - Albuquerque - Qualifikation | 2016/09/18 16:00 | Sabrina Santamaria v Chanel Simmonds | 6-4,7-6 |
| ITF Damen - Atlanta | 2016/09/15 18:40 | Michaella Krajicek v Chanel Simmonds | 6-3,6-2 |
| ITF Damen - Atlanta | 2016/09/14 18:15 | Chanel Simmonds v Marta H Gonzalez Encinas | 6-0,6-0 |
| Billie Jean King Cup | 2016/02/06 08:35 | Chanel Simmonds v Reka-Luca Jani | 0-6,3-6 |
| Billie Jean King Cup | 2016/02/03 08:45 | Sofia Shapatava v Chanel Simmonds | 7-5,6-4 |
| ITF Damen - Las Vegas | 2016/09/29 19:00 | Sesil Karatantcheva v Taylor Townsend | 0-6,6-7 |
| ITF Damen - Las Vegas | 2016/09/28 16:30 | Alize Lim v Sesil Karatantcheva | 5-7,3-6 |
| ITF Damen - Albuquerque | 2016/09/21 16:00 | Marie Bouzkova v Sesil Karatantcheva | 6-0,6-2 |
| WTA Quebec City Qual | 2016/09/10 22:40 | Danielle Lao v Sesil Karatantcheva | 2-6,6-2,6-2 |
| US Open 2016 Women | 2016/08/25 16:45 | Sesil Karatantcheva v Elise Mertens | 6-3,0-6,1-6 |
| US Open 2016 Women | 2016/08/23 17:10 | Sesil Karatantcheva v Rebecca Sramkova | 6-1,3-6,6-4 |
| Wimbledon - Damen - Quaifikation | 2016/06/21 17:15 | Sherazad Reix v Sesil Karatantcheva | 3-6,7-6,6-4 |
| WTA - Mallorca - Qualifikation | 2016/06/12 10:00 | Sorana Cirstea v Sesil Karatantcheva | 6-3,6-4 |