| ITF Women Stellenbosch | 12/07 10:50 | 26 | Chanel Simmonds v Joelle Kissell | 6-1,6-1 | |
| ITF Women Stellenbosch | 12/06 13:15 | 25 | Chanel Simmonds v Marlies Szupper | 6-4,6-4 | |
| ITF Women Stellenbosch | 12/03 12:00 | 29 | Chanel Simmonds v Salma Ewing | 6-4,4-6,4-6 | |
| ITF Women Stellenbosch | 12/02 08:00 | 28 | Chanel Simmonds v Lou Adler | 6-4,6-0 | |
| ITF Women Stellenbosch | 12/01 07:30 | 27 | Chanel Simmonds v Emilie L Gallagher | 6-1,6-1 | |
| ITF Women Stellenbosch | 11/30 09:40 | 26 | Chanel Simmonds v Laura Sainsbury | 6-0,6-3 | |
| ITF Women Stellenbosch | 11/29 11:00 | 25 | Chanel Simmonds v Lize-Alet Morkel | 6-0,6-1 | |
| ITF Women Stellenbosch | 11/26 08:00 | 29 | Chanel Simmonds v Naomi Totka | 6-1,6-0 | |
| ITF Women Stellenbosch | 11/25 07:30 | 28 | Chanel Simmonds v Nina Stadler | 6-0,6-0 | |
| ITF Women Stellenbosch | 11/24 09:25 | 27 | Chanel Simmonds v Petra Januskova | 6-4,6-1 | |
| ITF Women Stellenbosch | 11/23 07:00 | 26 | Chanel Simmonds v Lou Adler | 7-6,3-6,6-2 | |
| ITF Women Stellenbosch | 11/22 10:35 | 25 | [348] Chanel Simmonds v Madeleine Kobelt [337] | 6-1,6-2 | |
| ITF Women Dakar | 11/19 15:30 | 29 | [330] Chanel Simmonds v Valentini Grammatikopoulou [212] | 0-6,6-7 | |
| ITF Women Dakar | 11/18 14:10 | 28 | [330] Chanel Simmonds v Melanie Stokke [276] | 6-2,6-2 | |
| ITF Women Dakar | 11/17 11:00 | 27 | [190] Conny Perrin v Chanel Simmonds [330] | 6-7,4-6 | |
| ITF Women Dakar | 11/16 09:30 | 26 | Warona Mdlulwa v Chanel Simmonds | 0-6,1-6 | |
| ITF Women Dakar | 11/13 14:50 | 25 | Teresia Londol v Chanel Simmonds | 1-6,5-7 | |
| ITF Women Macon Qual | 10/22 15:30 | 54 | [422] Allie Kiick v Chanel Simmonds [314] | 7-5,6-1 | |
| ITF Women Florence | 10/19 14:00 | 26 | [314] Chanel Simmonds v Rebecca Peterson [211] | 1-6,0-6 | |
| ITF Women Florence | 10/17 15:30 | 25 | [286] Sarah-R Sekulic v Chanel Simmonds [314] | 4-6,6-3,0-6 | |
| ITF Women Sumter | 10/11 13:00 | 25 | [312] Chanel Simmonds v Sarah-R Sekulic [286] | 1-6,0-6 | |
| ITF Women Templeton | 09/26 19:30 | 25 | Chanel Simmonds v Anna K. Schmiedlova | 4-6,3-6 | |
| ITF Women Albuquerque | 09/20 18:50 | 25 | [251] Sanaz Marand v Chanel Simmonds [337] | 6-4,6-4 | |
| ITF Women Redding | 09/17 21:30 | 29 | [330] Chanel Simmonds v Robin Anderson [369] | 1-6,4-6 | |
| ITF Women Redding | 09/16 23:00 | 28 | Katie Swan v Chanel Simmonds | Retired | |
| ITF Women Redding | 09/15 19:00 | 27 | Urszula Radwanska v Chanel Simmonds | Walkover | |
| ITF Women Redding | 09/14 22:00 | 26 | [392] Natela Dzalamidze v Chanel Simmonds [330] | 3-6,4-6 | |
| ITF Women Redding | 09/13 17:30 | 25 | [446] Julia Elbaba v Chanel Simmonds [330] | 3-6,0-6 | |
| ITF Women Fort Worth | 08/04 15:00 | 27 | [284] Miharu Imanishi v Chanel Simmonds [330] | 6-3,6-2 | |
| ITF Women Fort Worth | 08/03 16:55 | 26 | [421] Alexa Guarachi v Chanel Simmonds [330] | 3-6,4-6 |