| ITF W25 Naples | 2019/11/17 14:00 | Anastasia Sysoeva v Eleonore Tchakarova | 6-2,6-7,10-5 |
| UTR Pro Tennis Series Florida Women | 2021/11/06 15:45 | Berta Bonardi v Anastasia Sysoeva | 6-2,1-6,5-6 |
| UTR Pro Tennis Series Florida Women | 2021/11/04 16:30 | Anastasia Sysoeva v Caroline Driscoll | 6-1,3-6,7-6 |
| UTR Pro Tennis Series Florida Women | 2021/11/03 17:00 | Anastasia Sysoeva v Jingyi Li | 6-1,6-1 |
| UTR Pro Tennis Series Florida Women | 2021/11/02 14:00 | Anastasia Sysoeva v Sophia C-Ignatiev | 6-0,6-0 |
| UTR Pro Tennis Series Florida Women | 2021/11/01 16:00 | Sonya Macavei v Anastasia Sysoeva | 3-6,6-3,6-2 |
| ITF W25 Florence | 2021/10/13 20:00 | Xiyu Wang v Anastasia Sysoeva | 6-2,6-0 |
| ITF W25 Florence | 2021/10/12 14:00 | Anastasia Sysoeva v Joelle Kissell | 6-1,6-3 |
| ITF W15 Hilton Head | 2021/10/05 21:30 | Raveena Kingsley v Anastasia Sysoeva | 7-5,6-1 |
| UTR Pro Tennis Series Florida Women | 2021/11/06 15:30 | Eleonore Tchakarova v Rushri Wijesundera | 7-6,6-3 |
| UTR Pro Tennis Series Florida Women | 2021/11/05 14:30 | Ariana Pursoo v Eleonore Tchakarova | 6-2,5-0 |
| UTR Pro Tennis Series Florida Women | 2021/11/04 15:00 | Meisha Kendall-Woseley v Eleonore Tchakarova | 2-6,5-7 |
| UTR Pro Tennis Series Florida Women | 2021/11/02 17:00 | Madison Bourguignon v Eleonore Tchakarova | 4-5 |
| UTR Pro Tennis Series Florida Women | 2021/11/01 13:00 | Eleonore Tchakarova v Verginie Tchakarova | 7-5,6-4 |
| ITF W15 Cancun | 2021/10/14 18:10 | Darja Semenistaja v Eleonore Tchakarova | 6-2,6-2 |
| ITF W15 Cancun | 2021/10/13 14:00 | Maria G Rivera Corado v Eleonore Tchakarova | 4-6,6-2,2-6 |
| ITF W15 Cancun | 2021/10/04 18:00 | Brandy Walker v Eleonore Tchakarova | 3-6,6-3,15-13 |