Stadium: Court 12 Round: 44 Ground: Hardcourt outdoor
| ITF W15 Cancun | 2021/09/26 17:30 | Maja Radenkovic v Gala Arangio | 6-0,6-2 |
| UTR Pro Tennis Series Sofia Women | 2021/09/02 11:30 | Eleonore Tchakarova v Maja Radenkovic | 6-2,6-3 |
| UTR Pro Tennis Series Sofia Women | 2021/09/01 08:00 | Maja Radenkovic v Nastja Kolar | 6-2,0-6,0-6 |
| UTR Pro Tennis Series Sofia Women | 2021/08/31 09:30 | Maja Radenkovic v Stela Peeva | 6-3,6-2 |
| UTR Pro Tennis Series Sofia Women | 2021/08/29 13:30 | Maja Radenkovic v Mirela Shkumbova | 6-3,4-6,5-2 |
| ITF W25 Vrnjacka Banja | 2021/08/16 09:50 | Maria Lota Kaul v Maja Radenkovic | 6-1,6-7,10-4 |
| ITF W25 Vrnjacka Banja | 2021/08/15 10:00 | Maja Radenkovic v Ekaterina Vishnevskaya | 6-2,7-6 |
| UTR Pro Tennis Series Beograd Women | 2021/07/18 13:00 | Maja Radenkovic v Cemre Anil | 3-6,1-2 |
| WTA Chicago | 2021/09/25 18:30 | Olga Govortsova v Adesuwa Osabuohien | 6-3,6-2 |
| Billie Jean King Cup | 2021/06/19 09:00 | Maria Siopacha v Adesuwa Osabuohien | 6-1,7-5 |
| Billie Jean King Cup | 2021/06/18 08:50 | Irena Muradyan v Adesuwa Osabuohien | 6-2,6-4 |
| Billie Jean King Cup | 2021/06/16 09:00 | Donika Bashota v Adesuwa Osabuohien | 1-6,4-6 |
| Billie Jean King Cup | 2021/06/15 09:00 | Iveta Dapkute v Adesuwa Osabuohien | 4-6,6-2,6-4 |
| ITF W15 Vilnius | 2021/06/07 09:00 | Adesuwa Osabuohien v Polina Ramenskaja | 5-7,2-6 |
| ITF W25 Potchefstroom | 2020/03/09 11:00 | Joanne Zuger v Adesuwa Osabuohien | 6-2,6-2 |
| ITF W25 Potchefstroom | 2020/03/09 07:00 | Aditi Sinha v Adesuwa Osabuohien | 0-6,2-6 |