| UTR Pro Tennis Series Florida Women | 2021/09/18 12:00 | Kent, Stephanie v Gabriel, Anais | 6-7,5-6 |
| UTR Pro Tennis Series Florida Women | 2021/09/16 16:30 | Kent, Stephanie v Ena Koike | 2-6,2-5 |
| UTR Pro Tennis Series Florida Women | 2021/09/15 12:00 | Katarina Kozarov v Kent, Stephanie | 6-3,6-1 |
| UTR Pro Tennis Series Florida Women | 2021/09/14 12:00 | Victoria Osuigwe v Kent, Stephanie | 2-6,6-6 |
| UTR Pro Tennis Series Florida Women | 2021/09/06 22:00 | Shelton, Emma v Kent, Stephanie | 6-3,5-3 |
| ITF W15 Cairo | 2021/07/21 13:10 | Tina Nadine Smith v Kent, Stephanie | 6-3,6-3 |
| ITF - W15 Monastir | 2021/07/14 10:00 | Julia Riera v Kent, Stephanie | 6-4,6-2 |
| ITF - W15 Monastir | 2021/07/05 11:30 | Bhunu, Valeria v Kent, Stephanie | 6-2,6-2 |
| UTR Pro Tennis Series Florida Women | 2021/09/17 22:30 | Brooke Pedersen v Darley, Cheri | 6-1,2-6,2-6 |
| UTR Pro Tennis Series Florida Women | 2021/09/15 13:30 | Eva Elbaz v Darley, Cheri | 7-5,5-4 |
| UTR Pro Tennis Series Florida Women | 2021/09/13 16:30 | Pierre-Louis, Kariann v Darley, Cheri | 6-4,6-4 |
| UTR Pro Tennis Series Barcelona Women | 2021/06/11 08:00 | Darley, Cheri v Cristina Flaquer | 4-6,3-6 |
| UTR Pro Tennis Series Barcelona Women | 2021/06/09 09:30 | Darley, Cheri v Darja Semenistaja | 1-6,3-6 |
| UTR Pro Tennis Series Barcelona Women | 2021/06/08 12:30 | Darley, Cheri v Iva Primorac | 1-6,3-5 |
| UTR Pro Tennis Series Barcelona Women | 2021/06/07 09:30 | Aran Teixido Garcia v Darley, Cheri | 6-0,5-3 |
| ITF W25 Platja D’Aro | 2021/05/16 07:30 | Darley, Cheri v Karman Kaur Thandi | 0-6,3-6 |