Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF - W15 Monastir | 2021/07/21 08:30 | Sysoeva, Anastasia v Eliessa Vanlangendonck | 1-6,4-6 |
| ITF - W15 Monastir | 2021/07/15 08:30 | Sysoeva, Anastasia v Eliessa Vanlangendonck | 6-7,3-6 |
| ITF - W15 Monastir | 2021/07/13 09:30 | Sysoeva, Anastasia v Leclercq, Anaelle | 6-2,6-0 |
| ITF - W15 Monastir | 2021/07/08 10:15 | Sysoeva, Anastasia v Valentina Ryser | 0-6,0-6 |
| ITF - W15 Monastir | 2021/07/06 10:10 | Zafeiri, Nefeli v Sysoeva, Anastasia | 3-6,3-6 |
| UTR Pro Tennis Series Florida Women | 2021/06/12 16:00 | Sysoeva, Anastasia v Pisareva, Alexandra | 4-6,6-7 |
| UTR Pro Tennis Series Florida Women | 2021/06/11 17:30 | Sysoeva, Anastasia v Nyjah Head | 6-3,5-3 |
| UTR Pro Tennis Series Florida Women | 2021/06/10 16:00 | Sysoeva, Anastasia v Johanna Silva | 3-6,2-5 |
| ITF W25 Evansville | 2021/07/15 14:00 | Katrina Scott v Jessica Failla | 7-5,7-5 |
| ITF W25 Evansville | 2021/07/14 14:15 | Sara Daavettila v Jessica Failla | 5-7,4-6 |
| ITF W25 Santo Domingo | 2021/06/09 15:35 | Jessica Failla v Kyoka Okamura | 6-4,6-2 |
| ITF W25 Santo Domingo | 2021/06/08 15:30 | Jessica Failla v Chavatipon, Charlotte | 7-6,6-1 |
| ITF W25 Santo Domingo | 2021/06/07 15:00 | Nefedova, Anastasia Evgenyevna v Jessica Failla | 5-7,6-1,5-10 |
| ITF W25 Santo Domingo | 2021/06/06 14:00 | Jessica Failla v Victoria Hu | 6-2,6-2 |
| ITF W25 Santo Domingo | 2021/06/04 12:50 | Conny Perrin v Jessica Failla | 6-4,5-7,6-3 |
| ITF W25 Santo Domingo | 2021/06/03 14:50 | Jessica Failla v Emiliana Arango | 6-2,6-2 |