Stadium: Court 9 Round: 54 Ground: Hardcourt outdoor
| ITF W15 Cancun | 2019/07/08 14:30 | Sysoeva, Anastasia v Maria Kozyreva | 6-7,1-6 |
| ITF W15 Cancun | 2019/07/03 13:30 | Sysoeva, Anastasia v Weedon, Kirsten-Andrea | 1-6,4-6 |
| ITF W15 Cancun | 2019/07/01 18:30 | Johnson, Bryn v Sysoeva, Anastasia | 2-6,1-6 |
| ITF W15 Cancun | 2019/07/01 15:00 | Sysoeva, Anastasia v Tkachenko, Diana | 6-3,7-6 |
| ITF W15 Cancun | 2019/06/24 14:30 | Verden Anderson, Camille v Sysoeva, Anastasia | 6-1,2-6,10-2 |
| Wesley Chapel, Singles Qualifying W-ITF-USA-26A | 2019/06/10 13:00 | Sysoeva, Anastasia v Megan McCray | 7-6,4-6,5-10 |
| ITF - W15 Antalya | 2019/05/14 07:15 | Ekaterina Ovcharenko v Sysoeva, Anastasia | 6-4,6-4 |
| ITF - W15 Antalya | 2019/05/07 08:00 | Ilay Yoruk v Sysoeva, Anastasia | 6-3,6-1 |
| ITF W15 Cancun | 2019/07/09 16:25 | Chikalkina, Anastasia v Weedon, Kirsten-Andrea | 0-6,1-6 |
| ITF W15 Cancun | 2019/07/01 18:30 | Chikalkina, Anastasia v Verden Anderson, Camille | 3-6,2-6 |
| Khimki, Singles W-ITF-RUS-04A | 2019/04/29 07:00 | Chikalkina, Anastasia v Husaric, Anita | 2-6,0-6 |
| Sharm El Sheikh, Singles W-WITF-EGY-09A | 2018/10/31 11:45 | Chikalkina, Anastasia v Eliz Maloney | 6-4,3-6,3-6 |
| Sharm El Sheikh, Singles W-WITF-EGY-09A | 2018/10/29 08:00 | Chantraine, Elisabeth v Chikalkina, Anastasia | 2-6,2-6 |
| Moscow, Singles W-WITF-RUS-05A | 2018/08/27 08:40 | Kruzhkova, Daria v Chikalkina, Anastasia | 7-5,6-2 |
| Moscow, Singles W-WITF-RUS-05A | 2018/08/26 07:00 | Chikalkina, Anastasia v Evgeniya Burdina | 7-6,6-3 |
| ITF Women Kazan | 2018/08/05 08:30 | Diana Demidova v Chikalkina, Anastasia | 6-0,6-7,6-1 |