| ITF Women Toronto | 2016/11/01 17:50 | Caitlin Whoriskey v Elise Mertens | 0-6,4-6 |
| ITF Women Poitiers | 2016/10/25 10:05 | Caitlin Whoriskey v Fiona Ferro | 6-3,1-6,3-6 |
| ITF Women Poitiers Qual | 2016/10/24 08:30 | Susanne Celik v Caitlin Whoriskey | 3-6,1-6 |
| ITF Women Poitiers Qual | 2016/10/23 11:55 | Caitlin Whoriskey v Virginie Razzano | 4-6,7-5,6-3 |
| ITF Women Poitiers Qual | 2016/10/22 09:25 | Caitlin Whoriskey v Greet Minnen | 1-6,6-4,6-3 |
| WTA Luxembourg Qual | 2016/10/17 08:00 | Caitlin Whoriskey v Tereza Smitkova | 5-7,2-6 |
| WTA Luxembourg Qual | 2016/10/16 08:00 | Elise Mertens v Caitlin Whoriskey | 5-7,0-6 |
| WTA Luxembourg Qual | 2016/10/15 10:20 | Caitlin Whoriskey v Claudia Coppola | 6-0,6-3 |
| ITF Women Waco Qual | 2016/11/06 16:00 | Karla D L L Montalvo v Jessica Hinojosa Gomez | 2-6,3-6 |