| ITF W15 Johannesburg | 09/28 08:00 | 28 | Chanel Simmonds v Maria Vittoria Viviani | 6-3,7-5 | |
| ITF W15 Johannesburg | 09/27 09:30 | 27 | Chanel Simmonds v Caroline Romeo | 7-6,6-1 | |
| ITF W15 Johannesburg | 09/26 08:00 | 26 | Chanel Simmonds v Stephanie Kent | Retired | |
| ITF W15 Johannesburg | 09/24 09:40 | 25 | Chanel Simmonds v Ntokozo Zungu | 6-0,6-0 | |
| ITF W60 Meitar | 09/11 14:00 | 26 | [220] Elitsa Kostova v Chanel Simmonds [387] | 6-2,6-3 | |
| ITF W60 Meitar | 09/10 07:00 | 25 | [332] Sofya Lansere v Chanel Simmonds [387] | 2-6,2-6 | |
| ITF W15 Sajur | 09/08 07:00 | 29 | Chanel Simmonds v Lina Glushko | 7-5,6-0 | |
| ITF W15 Sajur | 09/07 07:00 | 28 | [354] Alicia Barnett v Chanel Simmonds [383] | 6-7,3-6 | |
| ITF W15 Sajur | 09/06 07:00 | 27 | Chanel Simmonds v Victoria Muntean | Retired | |
| ITF W15 Sajur | 09/05 07:00 | 26 | Chanel Simmonds v Kristin Younes | 6-0,6-3 | |
| ITF W15 Sajur | 09/04 07:00 | 25 | Chanel Simmonds v Darya Shvartsmann | 6-3,6-3 | |
| ITF W25 Evansville | 07/26 15:00 | 27 | [425] Grace Min v Chanel Simmonds [396] | 6-4,6-3 | |
| ITF W25 Evansville | 07/25 17:50 | 26 | Katrina Scott v Chanel Simmonds | 2-6,4-6 | |
| ITF W25 Evansville | 07/24 14:00 | 25 | Jada Robinson v Chanel Simmonds | 3-6,1-6 | |
| ITF W60 Berkeley | 07/15 22:00 | 54 | [384] Chanel Simmonds v Victoria Duval [454] | 3-6,1-6 | |
| ITF W60 Honolulu | 07/10 21:30 | 25 | [482] Natasha Subhash v Chanel Simmonds [378] | 6-3,7-5 | |
| ITF W60 Honolulu | 07/09 20:30 | 54 | [378] Chanel Simmonds v Ramu Ueda [452] | 4-6,6-3,11-9 | |
| ITF W60 Honolulu | 07/08 20:00 | 54 | Chanel Simmonds v Chanelle Van Nguyen | 6-2,6-2 | |
| ITF W25 Daegu | 06/06 02:00 | 26 | Chanel Simmonds v Sunam Jeong | 2-6,1-6 | |
| ITF W25 Daegu | 06/05 04:55 | 25 | [355] Mai Hontama v Chanel Simmonds [417] | 4-6,4-6 | |
| ITF W25 Daegu | 06/04 01:00 | 54 | Chanel Simmonds v Hyojung Yea | 6-3,6-4 | |
| ITF W25 Daegu | 06/03 01:00 | 54 | Chanel Simmonds v Da Ye Kim | 6-1,6-2 | |
| ITF W25 Incheon | 05/31 02:00 | 27 | [304] Natalija Kostic v Chanel Simmonds [417] | 6-3,6-1 | |
| ITF W25 Incheon | 05/30 02:00 | 26 | [417] Chanel Simmonds v Maia Lumsden [319] | 6-2,7-5 | |
| ITF W25 Incheon | 05/29 02:50 | 25 | Yubean Lee v Chanel Simmonds | 1-6,0-6 | |
| ITF W25 Incheon | 05/28 01:00 | 54 | Chanel Simmonds v Yeong Won Jeong | 6-2,6-3 | |
| ITF W25 Incheon | 05/27 05:20 | 54 | Chanel Simmonds v Han-Bit Lee | 6-2,6-0 | |
| ITF W25 Goyang | 05/24 02:00 | 27 | [405] Chanel Simmonds v Natalija Kostic [304] | 6-7,3-6 | |
| ITF W25 Goyang | 05/23 02:00 | 26 | [443] Yuuki Tanaka v Chanel Simmonds [405] | 2-6,2-6 | |
| ITF W25 Goyang | 05/22 04:20 | 25 | [128] Ji-Hee Choi v Chanel Simmonds [405] | 1-6,7-6,4-6 |