Stadium: Court 2 Round: 44 Ground: Clay
| ITF Women Kazan | 2018/03/11 07:00 | Chikalkina, Anastasia v Treshcheva, Sofya | 6-7,1-6 |
| Moscow, Singles Qualifying W-WITF-RUS-05A | 2018/02/26 08:55 | Chikalkina, Anastasia v Mishina, Daria | 2-6,6-2,1-6 |
| Moscow, Singles Qualifying W-WITF-RUS-05A | 2018/02/25 11:00 | Kulikova, Yulia v Chikalkina, Anastasia | 2-6,2-6 |
| Antalya, Singles Qualifying W-WITF-TUR-08A | 2017/11/15 06:45 | Georgia Andreea Craciun v Chikalkina, Anastasia | 7-6,7-6 |
| Antalya, Singles Qualifying W-WITF-TUR-08A | 2017/11/13 07:15 | Veselova, Anastasia v Chikalkina, Anastasia | 6-4,6-7,1-6 |
| Antalya, Singles Qualifying W-WITF-TUR-08A | 2017/11/12 07:15 | Comlek, Azradeniz v Chikalkina, Anastasia | 6-7,1-6 |
| Antalya, Singles Qualifying W-WITF-TUR-08A | 2017/11/11 06:45 | Chikalkina, Anastasia v Mikhaylova, Maria | 6-1,6-2 |
| Antalya, Singles Qualifying W-WITF-TUR-08A | 2017/11/06 06:15 | Chikalkina, Anastasia v Maria Vittoria Viviani | 3-6,2-6 |
| Istanbul, Singles W-WITF-TUR-28B | 2017/08/02 08:00 | Kremer, Dana v Kuprina, Anastasiia | 6-0,6-3 |
| Istanbul, Singles W-WITF-TUR-28B | 2017/07/31 09:00 | Kuprina, Anastasiia v Kozyreva, Polina | 6-3,7-6 |
| Istanbul, Singles W-WITF-TUR-28B | 2017/07/30 08:00 | Mulalic, Ema v Kuprina, Anastasiia | 2-6,1-6 |