Stadium: Court 10 Round: 26 Ground: Hardcourt outdoor
| ITF W15 San Diego | 2023/06/13 17:30 | Simmonds, Chanel v Samantha Horwood | 6-3,6-2 |
| ITF W15 Rancho Santa Fe | 2023/06/01 20:00 | Haley Giavara v Simmonds, Chanel | 4-6,6-2,6-2 |
| ITF W15 Rancho Santa Fe | 2023/05/31 19:50 | Isabella Chhiv v Simmonds, Chanel | 2-6,2-6 |
| ITF W15 Rancho Santa Fe | 2023/05/30 16:00 | Simmonds, Chanel v Bianca Molnar | 6-0,6-2 |
| ITF W15 Rancho Santa Fe | 2023/05/29 17:30 | Alessandra Crump v Simmonds, Chanel | 0-6,0-6 |
| Billie Jean King Cup | 2022/07/08 08:15 | Gresi Bajri v Simmonds, Chanel | 1-6,2-6 |
| Billie Jean King Cup | 2022/07/07 09:15 | Simmonds, Chanel v Lina Gjorcheska | 2-6,0-6 |
| Billie Jean King Cup | 2022/07/05 10:15 | Simmonds, Chanel v Ekua Youri | 6-1,6-3 |
| ITF W15 San Diego | 2023/06/14 18:10 | Emily Deming v Megan McCray | 4-6,2-6 |
| ITF W15 Rancho Santa Fe | 2023/06/04 18:00 | Tian, Fangran v Megan McCray | 1-6,6-0,4-6 |
| ITF W15 Rancho Santa Fe | 2023/06/03 16:55 | Haley Giavara v Megan McCray | 6-4,1-6,2-6 |
| ITF W15 Rancho Santa Fe | 2023/06/01 19:35 | Anne Christine Lutkemeyer Obregon v Megan McCray | 4-6,4-6 |
| ITF W15 Rancho Santa Fe | 2023/05/31 16:55 | Alexis Nguyen v Megan McCray | 6-3,3-6,3-6 |
| UTR Pro California Women | 2023/05/07 19:19 | Hanna Chang v Megan McCray | 6-3,5-2 |
| UTR Pro California Women | 2023/05/06 17:00 | Alexia Jacobs v Megan McCray | 2-6,6-1,3-6 |
| UTR Pro California Women | 2023/05/05 20:00 | Megan McCray v Gianna Oboniye | 7-5,6-3 |