Stadium: Court 7 Round: 44 Ground: Clay
| Polish National Tour Women | 2020/08/22 12:05 | Olyanovskaya, Valeriya v Shoshyna, Anastasiya | 0-6,1-6 |
| ITF W25 Prague | 2020/09/06 10:30 | Sewing, Sofia v Olyanovskaya, Valeriya | 0-6,6-4,11-13 |
| Polish National Tour Women | 2020/08/22 12:05 | Olyanovskaya, Valeriya v Shoshyna, Anastasiya | 0-6,1-6 |
| Polish National Tour Women | 2020/08/16 11:30 | Oczachowska, Julia v Olyanovskaya, Valeriya | 6-4,6-4 |
| ITF - W15 Antalya | 2020/01/30 09:45 | Olyanovskaya, Valeriya v Georgia Andreea Craciun | 6-7,3-6 |
| ITF - W15 Antalya | 2020/01/29 11:35 | Olyanovskaya, Valeriya v Oleksandra Oliynykova | 1-6,6-2,6-0 |
| ITF - W15 Antalya | 2020/01/26 10:40 | Njiric, Silvia v Olyanovskaya, Valeriya | 0-6,2-6 |
| ITF - W15 Antalya | 2020/01/25 07:30 | Olyanovskaya, Valeriya v Zhibek Kulambayeva | 6-3,6-3 |
| ITF - W15 Antalya | 2020/01/24 07:00 | Honoka Kobayashi v Olyanovskaya, Valeriya | 0-6,0-6 |
| ITF W25 Prague | 2020/09/06 10:30 | Timea Jaruskova v Shoshyna, Anastasiya | 4-6,3-6 |
| Polish National Tour Women | 2020/08/25 08:00 | Weronika Falkowska v Shoshyna, Anastasiya | 3-6,4-6 |
| Polish National Tour Women | 2020/08/24 08:00 | Pola Wygonowska v Shoshyna, Anastasiya | 2-6,0-6 |
| Polish National Tour Women | 2020/08/23 12:55 | Kania, Paula v Shoshyna, Anastasiya | 6-2,3-6,3-6 |
| Polish National Tour Women | 2020/08/23 09:30 | Natalia Pietras v Shoshyna, Anastasiya | 2-6,0-6 |
| Polish National Tour Women | 2020/08/22 12:05 | Olyanovskaya, Valeriya v Shoshyna, Anastasiya | 0-6,1-6 |
| Polish National Tour Women | 2020/08/18 11:50 | Martyna Kubka v Shoshyna, Anastasiya | 3-6,0-6 |
| Polish National Tour Women | 2020/08/18 09:00 | Oczachowska, Julia v Shoshyna, Anastasiya | 2-6,3-6 |