Stadium: Clay Court 3 Round: 44 Ground: Clay
| ITF - W15 Héraklion | 2020/10/29 08:00 | Melania Delai v Olyanovskaya, Valeriya | 6-4,4-6,7-5 |
| ITF - W15 Héraklion | 2020/10/27 07:00 | Olyanovskaya, Valeriya v Kimmelmann, Julia | 6-3,4-6,11-9 |
| ITF - W15 Héraklion | 2020/10/26 08:00 | Olyanovskaya, Valeriya v Dshandshgava, Irina | 6-1,6-2 |
| ITF - W15 Sharm El Sheikh | 2020/10/07 11:15 | Anna Ulyashchenko v Olyanovskaya, Valeriya | 7-5,6-2 |
| ITF W25 Frydek Mistek | 2020/09/15 09:55 | Nikola Tomanova v Olyanovskaya, Valeriya | 1-6,7-6,10-5 |
| ITF W25 Frydek Mistek | 2020/09/14 08:00 | Olyanovskaya, Valeriya v Kajuru, Ange Oby | 6-3,6-4 |
| ITF W25 Frydek Mistek | 2020/09/13 10:00 | Olyanovskaya, Valeriya v Horackova, Gabriela | 6-0,6-3 |
| ITF W25 Prague | 2020/09/07 08:00 | Olyanovskaya, Valeriya v Shoshyna, Anastasiya | 7-6,2-6,5-10 |
| ITF - W15 Héraklion | 2020/10/26 10:00 | Orav, Saara v Kimmelmann, Julia | 6-2,2-6,7-10 |
| ITF - W15 Héraklion | 2020/10/25 12:00 | Koldobski, Koral v Orav, Saara | 3-6,1-6 |
| ITF W15 Liepaja | 2020/01/20 09:00 | Orav, Saara v Kajsa Rinaldo Persson | 4-6,6-7 |
| Parnu, Singles Qualifying W-ITF-EST-01A | 2019/11/05 12:50 | Pribylova, Anastasia v Orav, Saara | 6-0,6-0 |
| Parnu, Singles Qualifying W-ITF-EST-01A | 2019/07/18 15:50 | Orav, Saara v Fanny Ostlund | 6-2,2-6,5-7 |
| Parnu, Singles Qualifying W-ITF-EST-01A | 2019/07/18 09:05 | Orav, Saara v Dmitrieva, Sofia | 7-5,6-2 |
| Fed Cup, Groupe Mondial | 2019/02/08 09:00 | Marta Kostyuk v Orav, Saara | 6-3,6-0 |
| ITF Women Parnu | 2018/07/18 07:00 | Orav, Saara v Margarita Ignatjeva | 2-6,3-6 |