| ITF W25 Petange | 11/21 11:40 | 44 | Sara Pantelic v Chekanskaya, Anna | 6-4,3-6,4-10 | |
| ITF W25 Saint Etienne | 11/15 10:50 | 54 | 달트론, 에멜린 v Chekanskaya, Anna | 7-6,6-1 | |
| ITF W25 Saint Etienne | 11/14 08:00 | 54 | 라코토말라라, 마네바 v Chekanskaya, Anna | 3-6,2-6 | |
| ITF W15 Antalya | 11/09 11:40 | 25 | Chekanskaya, Anna v 포스펠로바, 알렉산드라 | 5-7,4-6 | |
| ITF W15 Antalya | 11/08 08:30 | 62 | Chekanskaya, Anna v Karolina Mrazikova | 6-0,6-0 | |
| ITF W15 Antalya | 11/07 12:20 | 62 | Chekanskaya, Anna v Brina Sulin | 6-2,6-2 | |
| ITF W15 Antalya | 11/06 05:30 | 62 | Chekanskaya, Anna v Zineb El Ouazzani | 6-4,6-3 | |
| ITF W15 Antalya | 11/03 08:40 | 26 | Chekanskaya, Anna v 에라이딘, 바사크 | 3-6,6-1,4-6 | |
| ITF W15 Antalya | 11/02 10:25 | 25 | Naroa Aranzabal v Chekanskaya, Anna | 5-7,4-6 | |
| ITF W25 Cherbourg | 10/09 11:50 | 54 | 쿠로비치, 타마라 v Chekanskaya, Anna | 3-6,7-6,10-8 | |
| ITF W15 Reims | 10/02 12:20 | 54 | Chekanskaya, Anna v Elizabete Brutane | 6-4,4-6,7-10 | |
| ITF W15 Dijon | 09/13 16:00 | 25 | 게트왈트, 파비엔 v Chekanskaya, Anna | 6-4,6-3 | |
| ITF W25 Antalya | 02/27 07:00 | 62 | 데미도바, 디아나 v Chekanskaya, Anna | 6-2,7-5 | |
| ITF W15 Antalya | 11/25 09:00 | 26 | 오르텐지, 자즈민 v Chekanskaya, Anna | 6-1,6-3 | |
| ITF W15 Antalya | 11/24 10:55 | 25 | Chekanskaya, Anna v 카르다바, 조지야 | 6-2,6-2 | |
| ITF W15 Antalya | 11/17 06:30 | 25 | Chekanskaya, Anna v Camilla Gennaro | 6-3,5-7,5-7 | |
| ITF W15 Antalya | 11/16 06:30 | 62 | Chekanskaya, Anna v Karolina Novakova | 6-1,6-1 | |
| ITF W15 Antalya | 11/15 06:30 | 62 | Chekanskaya, Anna v Uyar, Melis Ayda | 6-3,6-1 | |
| ITF W15 Antalya | 11/12 06:30 | 27 | Chekanskaya, Anna v 로브리치, 피아 | 5-7,2-6 | |
| ITF W15 Antalya | 11/11 06:30 | 26 | Chekanskaya, Anna v 라스쿠토바, 크세니아 | 4-6,6-4,7-6 | |
| ITF W15 Antalya | 11/10 08:50 | 25 | 드라호타 스자보, 돌카 v Chekanskaya, Anna | 6-1,3-6,1-6 | |
| ITF W15 Antalya | 11/09 06:30 | 62 | Chekanskaya, Anna v Shakirova, Dana | 6-1,6-3 | |
| ITF W15 Kazan | 10/13 10:05 | 25 | Chekanskaya, Anna v 데멘티에바, 엘리자베타 | 2-6,4-6 | |
| ITF W15 Kazan | 10/12 08:30 | 54 | Chekanskaya, Anna v Darya Zykova | 6-3,6-3 | |
| ITF W15 Moscow | 07/19 16:15 | 54 | Chekanskaya, Anna v Morozova, Elizaveta | 5-7,3-6 | |
| ITF W15 Shymkent | 05/31 06:40 | 54 | Chekanskaya, Anna v Sandugash Kenzhibayeva | 6-4,1-6,6-10 | |
| ITF W15 Shymkent | 05/26 12:15 | 25 | 사리포바, 사비나 v Chekanskaya, Anna | 2-6,6-2,6-3 | |
| ITF W15 Shymkent | 05/25 04:00 | 54 | Chekanskaya, Anna v 카림자노바, 야스미나 | 6-2,6-4 | |
| ITF W15 Antalya | 02/07 06:00 | 62 | 민테기 델 올모, 안 v Chekanskaya, Anna | 6-2,6-3 | |
| ITF W15 Antalya | 02/02 07:00 | 62 | Chekanskaya, Anna v 반 드 피어, 비키 | 3-6,6-7 |