Stadium: Court 4 Round: 54 Ground: Hardcourt indoor
| ITF W15 Moscow | 2021/07/19 16:15 | Chekanskaya, Anna v Morozova, Elizaveta | 5-7,3-6 |
| ITF W15 Shymkent | 2021/05/31 06:40 | Chekanskaya, Anna v Sandugash Kenzhibayeva | 6-4,1-6,6-10 |
| ITF W15 Shymkent | 2021/05/26 12:15 | 사리포바, 사비나 v Chekanskaya, Anna | 2-6,6-2,6-3 |
| ITF W15 Shymkent | 2021/05/25 04:00 | Chekanskaya, Anna v 카림자노바, 야스미나 | 6-2,6-4 |
| ITF W15 Antalya | 2021/02/07 06:00 | 민테기 델 올모, 안 v Chekanskaya, Anna | 6-2,6-3 |
| ITF W15 Antalya | 2021/02/02 07:00 | Chekanskaya, Anna v 반 드 피어, 비키 | 3-6,6-7 |
| ITF W15 Antalya | 2021/01/31 10:00 | 에크시바로바, 블라다 v Chekanskaya, Anna | 2-6,4-6 |
| ITF W15 Antalya | 2020/02/23 13:30 | Chekanskaya, Anna v 카제비치, 에나 | 6-7,4-6 |