| UTR Pro Tennis Series Sofia Women | 2021/09/01 06:30 | Tchakarova, Eleonore v Kraleva, Elena | 6-2,5-0 |
| UTR Pro Tennis Series Sofia Women | 2021/08/31 06:30 | Tchakarova, Eleonore v Mariya Poduraeva | 6-3,5-2 |
| UTR Pro Tennis Series Sofia Women | 2021/08/30 07:00 | Tchakarova, Eleonore v Julia Terziyska | 0-6,3-6 |
| ITF W60 Prerov | 2021/08/22 08:00 | Jessie Aney v Tchakarova, Eleonore | 6-1,6-0 |
| ITF W25 Vrnjacka Banja | 2021/08/16 08:00 | Veronika Erjavec v Tchakarova, Eleonore | 6-1,6-1 |
| ITF W25 Vrnjacka Banja | 2021/08/15 07:00 | Gvozdenovic, Sara v Tchakarova, Eleonore | 1-6,2-6 |
| ITF W25 Santo Domingo | 2021/06/07 14:00 | Zamburek, Ana Carmen v Tchakarova, Eleonore | 6-4,7-5 |
| ITF W25 Santo Domingo | 2021/05/31 14:00 | Emiliana Arango v Tchakarova, Eleonore | 6-4,6-2 |
| UTR Pro Tennis Series Sofia Women | 2021/09/01 08:00 | Maja Radenkovic v Kolar, Nastja | 6-2,0-6,0-6 |
| UTR Pro Tennis Series Sofia Women | 2021/08/31 09:30 | Maja Radenkovic v Peeva, Stela | 6-3,6-2 |
| UTR Pro Tennis Series Sofia Women | 2021/08/29 13:30 | Maja Radenkovic v Shkumbova, Mirela | 6-3,4-6,5-2 |
| ITF W25 Vrnjacka Banja | 2021/08/16 09:50 | Kaul, Maria Lota v Maja Radenkovic | 6-1,6-7,10-4 |
| ITF W25 Vrnjacka Banja | 2021/08/15 10:00 | Maja Radenkovic v Vishnevskaya, Ekaterina | 6-2,7-6 |
| UTR Pro Tennis Series Beograd Women | 2021/07/18 13:00 | Maja Radenkovic v Anil, Cemre | 3-6,1-2 |
| UTR Pro Tennis Series Beograd Women | 2021/07/18 07:00 | Maja Radenkovic v Ralitsa Alexandrova | 6-3,5-3 |
| UTR Pro Tennis Series Beograd Women | 2021/07/16 10:30 | Maja Radenkovic v Karola Patricia Bejenaru | 2-6,3-5 |