Stadium: Court 19 Round: 44
| ITF Women Khimki Qual | 2017/04/30 07:00 | Chikalkina, Anastasia v Диана Демидова | 5-7,3-6 |
| ITF Women Kazan | 2018/08/04 11:00 | Kazantseva, Daria v Диана Демидова | 0-6,0-6 |
| ITF Women Kazan | 2018/08/04 07:00 | Диана Демидова v Tselykovskaya, Anna | 6-1,6-1 |
| ITF Women Kazan | 2018/07/28 07:00 | Анастасия Сухотина v Диана Демидова | 7-5,7-6 |
| ITF Women Khimki Qual | 2018/04/28 13:05 | Екатерина Яшина v Диана Демидова | 6-2,7-5 |
| ITF Women Moscow | 2018/03/02 09:15 | Диана Демидова v Ольга Дорошина | 4-6,2-6 |
| ITF Women Moscow | 2018/03/01 08:30 | Тарасова, Алена v Диана Демидова | 6-2,4-6,4-6 |
| ITF Women Moscow | 2018/02/27 07:30 | Диана Демидова v Kharitonova, Anastasia | 7-5,6-3 |
| Moscow, Singles Qualifying W-WITF-RUS-05A | 2018/02/26 07:00 | Анастасия Сухотина v Диана Демидова | 2-6,6-7 |
| ITF Women Kazan | 2018/08/04 11:00 | Chikalkina, Anastasia v Тимофеева, Марина | 6-0,6-2 |
| ITF Women Kazan | 2018/08/04 07:00 | Chikalkina, Anastasia v Арина Соломатина | 7-5,6-1 |
| ITF Women Kazan | 2018/07/30 07:00 | Chikalkina, Anastasia v Анастасия Тихонова | 1-6,6-4,0-6 |
| ITF Women Minsk | 2018/06/13 09:10 | Bovy, Margaux v Chikalkina, Anastasia | 7-5,6-2 |
| ITF Women Minsk | 2018/06/12 07:00 | Анна Уколова v Chikalkina, Anastasia | 4-6,3-6 |
| Minsk, Singles Qualifying W-WITF-BLR-01A | 2018/06/11 10:05 | Chikalkina, Anastasia v Kasarzheuskaya, Anastasiya | 6-3,6-2 |
| Minsk, Singles Qualifying W-WITF-BLR-01A | 2018/06/10 09:30 | Chikalkina, Anastasia v Ksenia Kolesnikova | 6-4,6-1 |
| Minsk, Singles Qualifying W-WITF-BLR-01A | 2018/06/02 07:00 | Chikalkina, Anastasia v Анастасия Куприна | 3-6,6-4,3-6 |