Stadium: Court 3 Round: 44 Ground: Clay
| ITF W25 Daytona Beach | 2020/01/12 16:00 | Zimmermann, Kimberley v Tchakarova, Eleonore | 6-3,3-6,8-10 |
| ITF - W15 Antalya | 2019/12/16 06:30 | Manilova, Maria v Tchakarova, Eleonore | 6-4,6-2 |
| ITF W25 Naples | 2019/11/17 14:00 | Sysoeva, Anastasia v Tchakarova, Eleonore | 6-2,6-7,10-5 |
| ITF W25 Hilton Head Island | 2019/10/08 14:00 | Lauren Proctor v Tchakarova, Eleonore | 6-1,6-0 |
| 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 |
| ITF W25 Evansville | 2019/07/24 16:10 | Grace Min v Tchakarova, Eleonore | 6-1,6-1 |
| ITF W25 Evansville | 2019/07/23 14:00 | Collins, Kylie v Tchakarova, Eleonore | 6-1,5-7,2-10 |
| ITF W25 Daytona Beach | 2020/01/12 16:00 | Gailis, Rachel v Brantmeier, Reese | 0-6,6-3,10-6 |
| ITF W25 Naples | 2019/11/18 14:00 | Gailis, Rachel v Guttierez Carrasco, Maria | 3-6,1-6 |
| ITF W15 Cancun | 2019/11/06 17:05 | Jandric, Tea v Gailis, Rachel | 2-6,6-3,3-6 |
| ITF W15 Cancun | 2019/11/03 14:00 | Gailis, Rachel v Adrienn Nagy | 3-6,2-6 |
| ITF W15 Cancun | 2019/11/02 14:00 | Gailis, Rachel v Natarajan, Ramya | 6-2,6-2 |
| ITF W15 Cancun | 2019/11/01 13:55 | Gailis, Rachel v Ng, Taylor | 5-7,6-3,7-6 |
| ITF W15 Cancun | 2019/10/31 13:45 | Gailis, Rachel v Feder, Ambre | 6-0,6-1 |
| ITF W15 Cancun | 2019/10/30 14:00 | Sewing, Sofia v Gailis, Rachel | 0-6,6-3,2-6 |