Stadium: Court 12 Round: 54 Ground: Clay
| ITF W15 Gonesse | 2024/03/11 10:50 | Anna Chekanskaya v Camilia S Druz | 2-6,6-7 |
| ITF W25 Cherbourg | 2023/10/19 08:20 | Veronika Podrez v Anna Chekanskaya | 6-3,5-7,6-4 |
| ITF W25 Cherbourg | 2023/10/17 14:20 | Anna Chekanskaya v Alisa Baranovska | 5-7,6-1,6-3 |
| ITF W25 Cherbourg | 2023/10/16 15:55 | Flavie Brugnone v Anna Chekanskaya | 5-7,3-6 |
| ITF W25 Cherbourg | 2023/10/15 07:55 | Vanja Gudelj v Anna Chekanskaya | 6-7,1-6 |
| UTR Pro Beograd Women | 2023/10/12 06:00 | Anna Chekanskaya v Polina Bakhmutkina | 3-6,4-6 |
| UTR Pro Beograd Women | 2023/10/11 12:00 | Anna Chekanskaya v Ioana T Sava | 6-3,6-7,2-6 |
| UTR Pro Beograd Women | 2023/10/10 11:41 | Anna Chekanskaya v Ksenia Laskutova | 1-6,7-5,1-6 |