| ITF Women Berkeley | 07/18 22:20 | 25 | Chanel Simmonds v Pamela Montez | 6-1,6-3 | |
| ITF Women Honolulu | 07/12 21:25 | 26 | [316] Chanel Simmonds v Jessica Pegula [346] | 3-6,5-7 | |
| ITF Women Honolulu | 07/11 20:00 | 25 | Denise Starr v Chanel Simmonds | 0-6,1-6 | |
| ITF Women Essen | 06/12 10:30 | 25 | [351] Polina Leykina v Chanel Simmonds [280] | 6-4,6-1 | |
| WTA Nurnberg Qual | 05/19 09:50 | 45 | [315] Jesika Maleckova v Chanel Simmonds [287] | 6-4,6-1 | |
| ITF Women Rome | 05/10 11:50 | 27 | [314] Martina Di Giuseppe v Chanel Simmonds [287] | 6-4,6-2 | |
| ITF Women Rome | 05/09 09:00 | 26 | [243] Chantal Skamlova v Chanel Simmonds [287] | 6-3,4-6,1-6 | |
| ITF Women Rome | 05/07 10:00 | 25 | [287] Chanel Simmonds v Ipek Soylu [215] | 6-4,6-0 | |
| ITF Women Balatonboglar | 05/01 09:40 | 25 | [284] Chanel Simmonds v Naiktha Bains [353] | 4-6,6-7 | |
| ITF Women Wiesbaden | 04/24 12:50 | 25 | [308] Kimberley Zimmermann v Chanel Simmonds [284] | 2-6,6-3,6-3 | |
| 2018 Fed Cup | 04/19 09:10 | 29 | Chanel Simmonds v Elaine Genovese | 6-1,7-6 | |
| 2018 Fed Cup | 04/18 10:50 | - | [460] Mia Nicole Eklund v Chanel Simmonds [284] | 0-6,7-5,1-6 | |
| 2018 Fed Cup | 04/17 09:10 | 1 | Chanel Simmonds v Angella Okutoyi | 6-2,6-2 | |
| 2018 Fed Cup | 04/16 10:30 | - | [284] Chanel Simmonds v Danka Kovinic [121] | 4-6,5-7 | |
| ITF Women Jackson | 04/05 18:35 | 26 | [401] Chieh-Yu Hsu v Chanel Simmonds [284] | 6-4,6-4 | |
| ITF Women Jackson | 04/03 18:00 | 25 | [447] Quinn Gleason v Chanel Simmonds [284] | 2-6,1-6 | |
| ITF Women Orlando | 03/10 19:20 | 28 | Sophie Chang v Chanel Simmonds | 6-1,6-3 | |
| ITF Women Orlando | 03/09 16:00 | 27 | Aliona B. Zadoinov v Chanel Simmonds | 3-6,2-6 | |
| ITF Women Orlando | 03/08 15:00 | 26 | Catherine Leduc v Chanel Simmonds | 2-6,1-6 | |
| ITF Women Orlando | 03/07 17:25 | 25 | Angelina Zhuravleva v Chanel Simmonds | 3-6,4-6 | |
| ITF Women Surprise | 02/15 19:30 | 25 | Evgeniya Rodina v Chanel Simmonds | 6-2,6-1 | |
| ITF Women Surprise Qual | 02/13 17:30 | 62 | Chanel Simmonds v Clothilde De Bernardi | 6-4,7-6 | |
| ITF Women Surprise Qual | 02/12 17:00 | 62 | Chanel Simmonds v Julia Fisch | 6-1,6-1 | |
| ITF Women Surprise Qual | 02/11 20:00 | 62 | Chanel Simmonds v Emma Navarro | 6-4,6-3 | |
| ITF Women Midland Qual | 01/28 16:55 | 54 | Chanel Simmonds v Ann Li | 4-6,0-6 | |
| ITF Women Orlando | 01/16 20:35 | 25 | Chanel Simmonds v Maria Teresa Torro-Flor | 6-2,3-6,0-6 | |
| ITF Women Daytona Beach | 01/10 21:00 | 25 | Alexandra Perper v Chanel Simmonds | 4-6,7-6,10-7 | |
| ITF Women Stellenbosch | 12/10 08:00 | 29 | Chanel Simmonds v Lou Adler | 4-6,7-6,6-2 | |
| ITF Women Stellenbosch | 12/09 10:45 | 28 | Chanel Simmonds v Leonie Kung | 7-6,6-0 | |
| ITF Women Stellenbosch | 12/08 07:30 | 27 | Chanel Simmonds v Natalia Siedliska | 6-4,6-3 |