Stadium: Court 21 Round: 25 Ground: Clay
| 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 |
| ITF W25 Torino | 2021/07/05 11:00 | Jessica Bouzas Maneiro v Camilla Gennaro | 3-6,7-6,10-3 |
| ITF W15 L'Aquila | 2021/06/23 12:20 | Federica Prati v Camilla Gennaro | 7-5,3-6,7-5 |
| ITF W15 L'Aquila | 2021/06/22 07:00 | Elena Covi v Camilla Gennaro | 1-6,2-6 |
| ITF W15 L'Aquila | 2021/06/21 08:00 | Francesca Covi v Camilla Gennaro | 1-6,3-6 |
| ITF W15 L'Aquila | 2021/06/20 07:00 | Camilla Gennaro v Aline Thommen | 6-0,6-1 |