Stadium: Hard Court 3 Round: 44 Ground: Clay
| Antalya, Qualifications Simples W-ITF-TUR-35A | 2019/12/08 09:30 | Olyanovskaya, Valeriya v Oliwia Szymczuch | 6-3,6-3 |
| ITF - W15 Sharm El Sheikh | 2019/11/07 08:00 | Elena-Teodora Cadar v Olyanovskaya, Valeriya | 6-7,6-1,6-0 |
| ITF - W15 Sharm El Sheikh | 2019/11/06 08:00 | Olyanovskaya, Valeriya v Pitak, Aleksandra | 6-2,6-7,6-2 |
| ITF - W15 Sharm El Sheikh | 2019/11/04 08:00 | Olyanovskaya, Valeriya v Gorbunova, Mayya | 6-1,6-0 |
| Telavi, Singles W-ITF-GEO-04A | 2019/10/16 06:00 | Olyanovskaya, Valeriya v Anna Siskova | 2-6,0-6 |
| ITF W15 Chornomorsk | 2019/10/05 12:50 | Ardidiacono, Frederica v Olyanovskaya, Valeriya | 6-3,4-6,7-6 |
| ITF W15 Chornomorsk | 2019/10/04 13:10 | Olyanovskaya, Valeriya v Zhytelna, Yulia | 6-1,6-0 |
| ITF W15 Chornomorsk | 2019/10/03 10:15 | Bereznyak, Shelly v Olyanovskaya, Valeriya | 6-7,1-6 |
| Antalya, Qualifications Simples W-ITF-TUR-35A | 2019/12/08 09:30 | Peruhova, Lyuboslava v Olivia Gram | 0-6,0-6 |
| ITF - W15 Antalya | 2019/12/03 07:00 | Olivia Gram v Linda Sevcikova | 3-6,6-7 |
| ITF - W15 Antalya | 2019/12/02 07:00 | Olivia Gram v Lytneva, Anna | 4-6,6-3,10-8 |
| ITF - W15 Antalya | 2019/11/05 07:00 | Olivia Gram v Michalitsch, Alina | 6-3,0-6,9-11 |
| ITF - W15 Antalya | 2019/11/04 07:00 | Olivia Gram v Demidova, Liubov | 6-2,6-2 |
| ITF - W15 Antalya | 2019/10/29 07:00 | Tilbuerger, Jantje v Olivia Gram | 6-1,6-1 |
| ITF - W15 Antalya | 2019/10/28 07:00 | Glantz, Lola Mireille v Olivia Gram | 1-6,4-6 |
| ITF - W15 Antalya | 2019/10/24 07:00 | Noa Liauw A Fong v Olivia Gram | 6-0,6-1 |