Stadium: Court 4 Round: 54 Ground: Hardcourt indoor
| ITF W15 Moscow | 2021/07/19 16:15 | Anna Chekanskaya v Elizaveta Morozova | 5-7,3-6 |
| ITF W15 Shymkent | 2021/05/31 06:40 | Anna Chekanskaya v Sandugash Kenzhibayeva | 6-4,1-6,6-10 |
| ITF W15 Shymkent | 2021/05/26 12:15 | Sabina Sharipova v Anna Chekanskaya | 2-6,6-2,6-3 |
| ITF W15 Shymkent | 2021/05/25 04:00 | Anna Chekanskaya v Yasmina Karimjanova | 6-2,6-4 |
| ITF W15 Antalya | 2021/02/07 06:00 | Ane M D Olmo v Anna Chekanskaya | 6-2,6-3 |
| ITF W15 Antalya | 2021/02/02 07:00 | Anna Chekanskaya v Vicky Van De Peer | 3-6,6-7 |
| ITF W15 Antalya | 2021/01/31 10:00 | Vlada Ekshibarova v Anna Chekanskaya | 2-6,4-6 |
| ITF W15 Antalya | 2020/02/23 13:30 | Anna Chekanskaya v Ena Kajevic | 6-7,4-6 |