| WTA Honolulu | 11/24 01:30 | 26 | Danielle Collins v Crawford, Samantha | 1-6,5-7 | |
| WTA Honolulu | 11/22 22:00 | 25 | Erika Sema v Crawford, Samantha | 3-6,4-6 | |
| ITF Women Waco | 11/12 19:00 | 28 | Crawford, Samantha v Beatriz Haddad Maia | 2-6,4-6 | |
| ITF Women Waco | 11/11 20:35 | 27 | Crawford, Samantha v Collins, Danielle | 6-4,6-2 | |
| ITF Women Waco | 11/10 17:00 | 26 | Crawford, Samantha v Buzarnescu, Mihaela | 7-6,6-4 | |
| ITF Women Waco | 11/09 17:30 | 25 | Crawford, Samantha v Michaella Krajicek | 6-4,7-6 | |
| ITF Women Scottsdale | 11/02 16:30 | 25 | Sofia Kenin v Crawford, Samantha | 7-5,6-7,6-4 | |
| ITF Women Macon | 10/27 16:20 | 26 | Crawford, Samantha v Kayla Day | 3-6,2-6 | |
| ITF Women Macon | 10/25 18:35 | 25 | Crawford, Samantha v Michaella Krajicek | 7-5,7-6 | |
| WTA Hong Kong | 10/11 08:35 | 25 | Jankovic, Jelena v Crawford, Samantha | 6-3,6-1 | |
| WTA Beijing Qual | 09/30 03:00 | 45 | Crawford, Samantha v Rodina, Evgeniya | 4-6,5-7 | |
| WTA Wuhan Qual | 09/24 08:45 | 46 | Crawford, Samantha v Heather Watson | 6-7,2-6 | |
| WTA Wuhan Qual | 09/23 10:45 | 45 | Klepac, Andreja v Crawford, Samantha | 2-6,1-6 | |
| WTA Wuhan Qual | 09/23 08:30 | 45 | Niculescu, Monica v Crawford, Samantha | Cancelled | |
| Quebec City, Canada | 09/14 19:20 | 26 | Lauren Davis v Crawford, Samantha | 6-4,6-1 | |
| Quebec City, Canada | 09/12 15:00 | 25 | Ysaline Bonaventure v Crawford, Samantha | 6-7,7-6,4-6 | |
| US Open 2016 Women | 08/29 15:00 | 23 | Crawford, Samantha v Bencic, Belinda | 7-6,3-6,4-6 | |
| WTA Montreal Qual | 07/23 14:00 | 44 | Andreescu, Bianca Vanessa v Crawford, Samantha | 7-6,7-5 | |
| Wimbledon Women | 06/30 13:55 | 24 | Safarova, Lucie v Crawford, Samantha | 6-3,6-4 | |
| Wimbledon Women | 06/27 12:15 | 23 | Crawford, Samantha v Kania, Paula | 7-5,6-3 |