Stadium: Court 4 Round: 44 Ground: Clay
| ITF W15 Prokuplje | 2021/06/27 07:00 | Gvozdenovic, Sara v Fernandez, Bianca Jolie | 0-6,2-6 |
| ITF W15 Banja Luka | 2021/05/31 09:30 | Mia Ristic v Gvozdenovic, Sara | 6-1,6-2 |
| ITF - W15 Antalya | 2020/12/15 11:00 | Maria Sara Popa v Gvozdenovic, Sara | 6-0,6-2 |
| ITF - W15 Antalya | 2020/12/06 07:00 | Maria Sara Popa v Gvozdenovic, Sara | 7-6,6-2 |
| ITF - W15 Antalya | 2020/11/30 11:30 | Sofia Milatova v Gvozdenovic, Sara | 6-2,6-3 |
| ITF - W15 Antalya | 2020/11/29 07:00 | Anastasia Mozgaleva v Gvozdenovic, Sara | 4-6,1-6 |
| ITF Women Varna | 2020/09/07 07:30 | Shkumbova, Mirela v Gvozdenovic, Sara | 6-3,7-5 |
| ITF W15 Otocec | 2020/09/01 08:45 | Gvozdenovic, Sara v Chanel Janssen | 3-6,5-7 |
| ITF W25 Santo Domingo | 2021/06/07 14:00 | Ana C Zamburek 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 |
| ITF W25 Santo Domingo | 2021/05/30 14:00 | Maria Gell v Tchakarova, Eleonore | 0-6,1-6 |
| ITF W25 Salinas | 2021/05/10 16:35 | Tchakarova, Eleonore v Victoria Rodriguez | 2-6,5-7 |
| ITF W25 Salinas | 2021/05/04 14:00 | Tchakarova, Eleonore v Lia Karatancheva | 5-7,1-6 |
| ITF W25 Salinas | 2021/05/03 14:00 | Jacqueline Cabaj Awad v Tchakarova, Eleonore | 4-6,7-6,6-10 |
| ITF W25 Salinas | 2021/05/02 14:00 | Tchakarova, Eleonore v Appel, Madison | 6-2,6-4 |
| ITF W15 Cancun | 2020/03/09 17:00 | Tchakarova, Eleonore v Tchakarova, Verginie | 3-6,3-6 |