Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| 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 |
| ITF W15 Chornomorsk | 2019/10/01 08:55 | Klymenko, Anastasiya v Olyanovskaya, Valeriya | 1-6,1-6 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/31 08:45 | Olyanovskaya, Valeriya v Daria Kudashova | 3-6,1-6 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/30 06:00 | Olyanovskaya, Valeriya v Iveta Dapkute | 6-2,7-6 |
| ITF - W15 Sharm El Sheikh | 2019/10/10 09:20 | Pradova, Martina v Pitak, Aleksandra | 6-2,3-6,6-4 |
| ITF - W15 Sharm El Sheikh | 2019/10/08 11:10 | Pang, Sarah v Pitak, Aleksandra | 0-6,2-6 |
| ITF - W15 Sharm El Sheikh | 2019/10/05 08:00 | Pitak, Aleksandra v Dasha Ivanova | 6-1,2-6,2-6 |
| ITF - W15 Sharm El Sheikh | 2019/10/04 08:00 | Cataldi, Taylor v Pitak, Aleksandra | 2-6,6-7 |
| ITF - W15 Sharm El Sheikh | 2019/10/03 09:25 | Romana Cisovska v Pitak, Aleksandra | 2-6,3-6 |
| ITF - W15 Sharm El Sheikh | 2019/10/02 13:25 | Akiyama, Minami v Pitak, Aleksandra | 2-6,1-6 |
| ITF W25 Roehampton | 2019/09/24 08:30 | Arn, Greta v Pitak, Aleksandra | 6-1,6-0 |
| ITF W25 Roehampton | 2019/09/23 13:05 | Emily Appleton v Pitak, Aleksandra | 6-4,2-6,4-10 |