Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| ITF W25 Johannesburg | 2021/09/14 09:45 | Amina Anshba v Simmonds, Chanel | 4-6,4-6 |
| Billie Jean King Cup | 2021/06/19 10:15 | Bowtell, Anna v Simmonds, Chanel | 2-6,4-6 |
| Billie Jean King Cup | 2021/06/18 10:15 | Simmonds, Chanel v Helene Pellicano | 6-0,2-6,4-6 |
| Billie Jean King Cup | 2021/06/17 10:30 | Simmonds, Chanel v Ratkovic, Divna | 6-1,6-0 |
| Billie Jean King Cup | 2021/06/16 10:15 | Simmonds, Chanel v Umayra Hashimova | 6-1,6-0 |
| Billie Jean King Cup | 2021/06/15 10:30 | Simmonds, Chanel v Georgina Moolman | 6-0,6-1 |
| ITF W25 Potchefstroom | 2021/02/20 08:00 | Carol Zhao v Simmonds, Chanel | 6-4,6-4 |
| ITF W25 Potchefstroom | 2021/02/19 07:55 | Simmonds, Chanel v Jesika Maleckova | 7-5,3-6,6-4 |
| ITF W25 Johannesburg | 2021/09/15 10:10 | Heike Janse Van Vuuren v Matilda Mutavdzic | 2-6,4-6 |
| ITF W25 Johannesburg | 2021/09/13 14:30 | Caroline Romeo v Matilda Mutavdzic | 1-6,3-6 |
| ITF W25 Johannesburg | 2021/09/13 11:10 | Lieberman, Shachf v Matilda Mutavdzic | 0-6,1-6 |
| ITF W25 Vigo | 2021/08/24 08:00 | Jessica Failla v Matilda Mutavdzic | 1-6,6-2,10-6 |
| ITF W25 Vigo | 2021/08/23 11:00 | Luana Plaza Araujo v Matilda Mutavdzic | 1-6,1-6 |
| ITF - W15 Monastir | 2021/08/12 08:00 | Matilda Mutavdzic v Raveena Kingsley | 1-6,1-6 |
| Wimbledon Women | 2021/06/23 12:25 | Matilda Mutavdzic v Ana Konjuh | 1-6,2-6 |
| ITF W100 Nottingham | 2021/06/16 10:00 | Xinyu Wang v Matilda Mutavdzic | 7-5,6-1 |