| ITF - W25 Changwon | 05/19 01:30 | 29 | [285] Ya-Hsuan Lee v Chanel Simmonds [349] | 3-6,5-7 | |
| ITF - W25 Changwon | 05/18 03:00 | 28 | [493] Leonie Kung v Chanel Simmonds [349] | 1-6,6-2,3-6 | |
| ITF - W25 Changwon | 05/17 02:00 | 27 | Eunhye Lee v Chanel Simmonds | 6-7,2-6 | |
| ITF - W25 Changwon | 05/16 01:00 | 26 | [349] Chanel Simmonds v Natalija Kostic [299] | 7-6,6-1 | |
| ITF - W25 Changwon | 05/14 03:00 | 25 | [349] Chanel Simmonds v Daria Mishina [390] | 6-1,6-0 | |
| ITF - W15 Antalya | 04/27 07:30 | 28 | Chanel Simmonds v Anna Kubareva | 3-6,1-6 | |
| ITF - W15 Antalya | 04/26 09:20 | 27 | Chanel Simmonds v Ekaterina Ovcharenko | 6-1,6-0 | |
| ITF - W15 Antalya | 04/25 09:40 | 26 | Chanel Simmonds v Vivien Sandberg | 6-2,6-0 | |
| ITF - W15 Antalya | 04/24 11:00 | 25 | Chanel Simmonds v Justine Pysson | 6-0,6-3 | |
| ITF - W15 Antalya | 04/21 08:00 | 29 | Chanel Simmonds v Laura Schaeder | 6-2,6-1 | |
| ITF - W15 Antalya | 04/20 07:30 | 28 | Chanel Simmonds v Mariana Drazic | 6-3,6-1 | |
| ITF - W15 Antalya | 04/19 07:30 | 27 | Chanel Simmonds v Eliessa Vanlangendonck | 6-1,6-0 | |
| ITF - W15 Antalya | 04/18 09:00 | 26 | Chanel Simmonds v Gabriela Nicole Tatarus | 6-1,6-2 | |
| ITF - W15 Antalya | 04/17 07:00 | 25 | Chanel Simmonds v Alexa Pirok | 6-0,6-1 | |
| ITF - W25 Santa Margherita | 04/01 12:00 | 54 | Federica Bilardo v Chanel Simmonds | 5-7,6-2,10-7 | |
| ITF - W25 Santa Margherita | 03/25 14:30 | 45 | Federica Rossi v Chanel Simmonds | 6-4,6-3 | |
| 2019 Fed Cup | 02/08 16:45 | - | Francisca Jorge v Chanel Simmonds | 6-1,6-3 | |
| 2019 Fed Cup | 02/07 17:35 | - | Maya Tahan v Chanel Simmonds | 4-6,4-6 | |
| 2019 Fed Cup | 02/06 16:15 | 1 | [99] Mandy Minella v Chanel Simmonds [488] | 6-1,6-1 | |
| ITF Women Toronto | 10/31 17:55 | 25 | [316] Quirine Lemoine v Chanel Simmonds [370] | Retired | |
| ITF Women Macon | 10/21 14:00 | 54 | Chanel Simmonds v Hailey Baptiste | 6-3,3-6,3-6 | |
| ITF Women Florence | 10/17 18:05 | 25 | [363] Chanel Simmonds v Francoise Abanda [219] | 0-6,6-2,2-6 | |
| ITF Women Charleston | 10/04 14:00 | 26 | Chanel Simmonds v Hailey Baptiste | 1-6,1-6 | |
| ITF Women Charleston | 10/03 16:30 | 25 | Chanel Simmonds v Chanelle Van Nguyen | 6-3,6-3 | |
| ITF Women Templeton | 09/23 17:00 | 54 | [332] Chanel Simmonds v Cornelia Lister [112] | 5-7,4-6 | |
| ITF Women Lubbock | 09/19 17:00 | 26 | [279] Emina Bektas v Chanel Simmonds [332] | 6-2,6-3 | |
| ITF Women Lubbock | 09/17 19:20 | 25 | Chanel Simmonds v Anastasia Nefedova | 6-3,6-1 | |
| ITF Women Lexington | 08/01 20:15 | 25 | [321] Chanel Simmonds v Jaimee Fourlis [205] | 6-4,4-6,4-6 | |
| ITF Women Ashland | 07/24 15:30 | 25 | [322] Jovana Jaksic v Chanel Simmonds [296] | 6-2,6-1 | |
| ITF Women Berkeley | 07/19 19:00 | 26 | [154] Jamie Loeb v Chanel Simmonds [313] | 6-4,6-1 |