Round: 26 Ground: Hardcourt indoor
| ITF Women Stillwater | 2016/09/28 15:00 | Francesca Di Lorenzo v Yuliya Beygelzimer | 7-6,6-7,2-6 |
| US Open 2016 Women | 2016/08/23 16:35 | Francesca Di Lorenzo v Kristie Ahn | 6-1,3-6,4-6 |
| ITF Women Macon | 2016/10/25 17:20 | Alexa Guarachi v Chanel Simmonds | 4-6,0-6 |
| ITF Women Redding | 2016/10/05 20:25 | Chanel Simmonds v Sesil Karatantcheva | 3-6,2-6 |
| ITF Women Las Vegas Qual | 2016/09/27 16:30 | Julia Elbaba v Chanel Simmonds | 6-2,4-6,6-3 |
| ITF Women Las Vegas Qual | 2016/09/26 16:30 | Ai Wen Zhu v Chanel Simmonds | 1-6,0-6 |
| ITF Women Las Vegas Qual | 2016/09/25 21:50 | Jessica Wacnik 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 Marta H Gonzalez Encinas | 6-0,6-0 |