Stadium: Court 4 Round: 44 Ground: Clay
| ITF W15 Cancun | 2020/03/09 17:00 | Tchakarova, Eleonore v Tchakarova, Verginie | 3-6,3-6 |
| ITF W25 Hilton Head Island | 2019/10/07 16:00 | Tchakarova, Verginie v Tchakarova, Eleonore | 4-6,3-6 |
| ITF W15 Vrnjacka Banja | 2019/08/25 09:00 | Tchakarova, Verginie v Tchakarova, Eleonore | 2-6,6-2,11-9 |
| UTR Pro Tennis Series Sofia Women | 2021/09/02 11:30 | Vaneva, Zinovia v Tchakarova, Verginie | 6-3,4-6,6-4 |
| UTR Pro Tennis Series Sofia Women | 2021/09/01 06:30 | Tchakarova, Verginie v Sara Mikaca | 6-3,6-2 |
| UTR Pro Tennis Series Sofia Women | 2021/08/30 08:30 | Tchakarova, Verginie v Velizara Fileva | 6-1,7-6 |
| UTR Pro Tennis Series Sofia Women | 2021/08/29 13:30 | Tchakarova, Verginie v Silvia Maria Costache | 4-6,4-6 |
| ITF W60 Prerov | 2021/08/22 10:00 | Tchakarova, Verginie v Tomajkova, Kristyna | 3-6,4-6 |
| ITF W25 Vrnjacka Banja | 2021/08/16 11:00 | Tchakarova, Verginie v Lia Karatancheva | 1-6,3-6 |
| ITF W25 Vrnjacka Banja | 2021/08/15 13:00 | Tchakarova, Verginie v Zupancic, Nika | 6-4,6-4 |
| ITF W25 Santo Domingo | 2021/06/07 13:00 | Tchakarova, Verginie v Collins, Kylie | 2-6,3-6 |
| UTR Pro Tennis Series Sofia Women | 2021/09/03 10:00 | Amariei I Dalina v Tchakarova, Eleonore | 3-6,6-3,6-0 |
| UTR Pro Tennis Series Sofia Women | 2021/09/02 11:30 | Tchakarova, Eleonore v Maja Radenkovic | 6-2,6-3 |
| 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 |