Stadium: Clay 1 Round: 26 Ground: Clay
| ITF Women Heraklion | 2018/11/08 09:45 | Oleksandra Oliynykova v Darya Astakhova | 3-6,6-4,5-7 |
| ITF W15 Heraklion | 2019/05/08 07:00 | Martina Pradova v Darya Astakhova | 2-6,4-6 |
| ITF W25 Kazan | 2019/01/21 07:00 | Marianna Zakarlyuk v Darya Astakhova | 3-6,6-2,10-8 |
| ITF Women Heraklion | 2018/11/13 07:30 | Alexandra Petric v Darya Astakhova | 4-6,2-6 |
| ITF Women Heraklion | 2018/11/11 12:00 | Darya Astakhova v Anna Ureke | 2-6,6-1,2-6 |
| ITF Women Heraklion | 2018/11/10 10:20 | Darya Astakhova v Oana Gavrila | 7-5,6-2 |
| ITF Women Heraklion | 2018/11/08 09:45 | Oleksandra Oliynykova v Darya Astakhova | 3-6,6-4,5-7 |
| ITF Women Heraklion | 2018/11/06 09:05 | Haley Giavara v Darya Astakhova | 4-6,6-4,2-6 |
| ITF Women Heraklion | 2018/11/05 07:30 | Darya Astakhova v Tamara Malesevic | 6-2,6-2 |
| ITF W15 Heraklion | 2019/05/08 07:00 | Ambre Feder v Oleksandra Oliynykova | 6-0,0-6,4-6 |
| ITF W15 Antalya | 2019/02/18 07:00 | Oleksandra Oliynykova v Anastasia Reimchen | 2-6,6-7 |
| ITF W15 Antalya | 2019/02/15 06:30 | Oleksandra Oliynykova v Jessica Ho | 4-6,1-6 |
| ITF W15 Antalya | 2019/02/14 07:00 | Carole Monnet v Oleksandra Oliynykova | 6-4,1-6,3-6 |
| ITF W15 Antalya | 2019/02/12 07:00 | Oleksandra Oliynykova v Fanny Ostlund | 6-2,6-1 |
| ITF W15 Antalya | 2019/02/11 07:00 | Oleksandra Oliynykova v Elena Di Battista | 6-1,6-1 |
| ITF W25 Hong Kong | 2019/01/02 05:15 | Naomi Broady v Oleksandra Oliynykova | 6-1,6-2 |
| ITF Women Heraklion | 2018/11/18 11:30 | Oleksandra Oliynykova v Ania Hertel | 7-6,7-6 |