Round: 25 Ground: Hardcourt indoor
| WTA Hong Kong | 2016/10/11 08:35 | Jankovic, Jelena v Crawford, Samantha | 6-3,6-1 |
| WTA Beijing Qual | 2016/09/30 03:00 | Crawford, Samantha v Rodina, Evgeniya | 4-6,5-7 |
| WTA Wuhan Qual | 2016/09/24 08:45 | Crawford, Samantha v Heather Watson | 6-7,2-6 |
| WTA Wuhan Qual | 2016/09/23 10:45 | Klepac, Andreja v Crawford, Samantha | 2-6,1-6 |
| Quebec City, Canada | 2016/09/14 19:20 | Lauren Davis v Crawford, Samantha | 6-4,6-1 |
| Quebec City, Canada | 2016/09/12 15:00 | Ysaline Bonaventure v Crawford, Samantha | 6-7,7-6,4-6 |
| US Open 2016 Women | 2016/08/29 15:00 | Crawford, Samantha v Bencic, Belinda | 7-6,3-6,4-6 |
| WTA Montreal Qual | 2016/07/23 14:00 | Bianca Andreescu v Crawford, Samantha | 7-6,7-5 |
| ITF Women Las Vegas | 2016/09/29 16:30 | Sachia Vickery v Michaella Krajicek | 2-6,6-4,6-2 |
| ITF Women Las Vegas | 2016/09/28 18:00 | Michaella Krajicek v Hibi, Mayo | 6-1,6-4 |
| Albuquerque, Simples W-WITF-USA-30A | 2016/09/23 17:30 | Michaella Krajicek v Alison Van Uytvanck | 2-6,4-6 |
| Albuquerque, Simples W-WITF-USA-30A | 2016/09/22 17:30 | Michaella Krajicek v Renata Zarazua | 6-2,6-3 |
| Albuquerque, Simples W-WITF-USA-30A | 2016/09/21 17:50 | Michaella Krajicek v Usue Maitane Arconada | 6-3,6-0 |
| ITF Women Atlanta | 2016/09/16 16:10 | Michaella Krajicek v Ahn, Kristie | 6-1,3-6,3-6 |
| ITF Women Atlanta | 2016/09/15 18:40 | Michaella Krajicek v Chanel Simmonds | 6-3,6-2 |
| ITF Women Atlanta | 2016/09/13 15:30 | Michaella Krajicek v Sophie Chang | 6-2,6-4 |