| UTR Pro Tennis Series Florida Women | 2021/06/08 13:00 | Kianah Motosono v Johanna Silva | 6-7,1-6 |
| UTR Pro Tennis Series Florida Women | 2021/06/07 14:30 | Kianah Motosono v Maria Kononova | 0-6,3-5 |
| UTR Pro Tennis Series Florida Women | 2021/06/08 17:30 | Maria Kononova v Anastasia Sysoeva | 6-4,2-6,6-3 |
| UTR Pro Tennis Series Florida Women | 2021/06/05 13:30 | Anastasia Sysoeva v Carolyn Ansari | 2-6,3-6 |
| UTR Pro Tennis Series Florida Women | 2021/06/04 13:30 | Gabriella Broadfoot v Anastasia Sysoeva | 4-6,5-6 |
| UTR Pro Tennis Series Florida Women | 2021/06/03 14:30 | Alexandra Pisareva v Anastasia Sysoeva | 6-2,6-0 |
| UTR Pro Tennis Series Florida Women | 2021/06/01 18:00 | Kathryn Treiber v Anastasia Sysoeva | 6-4,3-6,1-5 |
| ITF W25 Pelham | 2021/05/16 17:30 | Liga Dekmeijere v Anastasia Sysoeva | 3-6,6-0,11-9 |
| ITF W25 Naples | 2021/05/04 16:45 | Anna Siskova v Anastasia Sysoeva | 6-1,6-2 |
| ITF W25 Naples | 2021/05/03 14:00 | Dhruthi Tatachar Venugopal v Anastasia Sysoeva | 1-6,2-6 |