Round: 26 Ground: Hardcourt outdoor
| Republica Ceha - Extraliga | 2016/11/02 06:54 | Chanel Simmonds v Minette Van Vreden | 6-0,3-0 |
| ITF Women Stellenbosch | 2016/11/01 23:00 | Chanel Simmonds v Nadia Van Heerden | 6-0,6-0 |
| ITF Women Macon | 2016/10/27 14:00 | Francesca Di Lorenzo v Chanel Simmonds | 6-4,6-2 |
| 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 Stellenbosch | 2016/11/01 23:00 | Alice Gillan v Annick Verhaar | 6-3,6-0 |
| ITF Women Stellenbosch Qual | 2016/10/30 23:00 | Alice Gillan v Sarah Pang | 6-0,6-0 |
| ITF Women Loughborough | 2016/10/26 09:00 | Alice Gillan v Kelly Versteeg | 0-6,1-6 |
| ITF Women Roehampton | 2016/09/27 11:25 | Eva Siska v Alice Gillan | 7-5,6-2 |
| ITF Women Roehampton | 2016/09/25 12:30 | Ella Taylor v Alice Gillan | 3-6,4-6 |
| ITF Women Nottingham | 2016/09/19 10:00 | Alice Gillan v Natasha Hillyer | 6-4,2-6,2-6 |
| ITF Women Nottingham | 2016/09/18 09:30 | Alice Gillan v Corina Mader | 7-6,6-1 |