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