Stadium: Court 4 Round: 28 Ground: Hardcourt outdoor
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/30 06:00 | Olyanovskaya, Valeriya v Iveta Dapkute | 6-2,7-6 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/29 06:00 | Jacqueline Cabaj Awad v Olyanovskaya, Valeriya | 4-6,6-1,1-6 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/28 09:30 | Gagoshidze, Tamari v Olyanovskaya, Valeriya | 3-6,1-6 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/26 10:30 | Helbet, Julia v Olyanovskaya, Valeriya | 2-6,1-6 |
| ITF Women Torun Qual | 2018/06/24 12:00 | Ksenia Laskutova v Olyanovskaya, Valeriya | 6-1,6-7,6-3 |
| Minsk, Singles Qualifying W-WITF-BLR-01A | 2017/11/20 07:00 | Olyanovskaya, Valeriya v Fisch, Julia | 6-4,4-6,6-2 |
| Minsk, Singles Qualifying W-WITF-BLR-01A | 2017/11/19 09:30 | Olyanovskaya, Valeriya v Pryts, Veranika | 6-3,6-2 |
| Batumi, Singles W-WITF-GEO-03A | 2016/08/30 06:00 | Ekaterine Gorgodze v Olyanovskaya, Valeriya | 6-3,6-2 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/30 06:00 | Daria Kudashova v Pospelova, Aleksandra | 6-1,6-4 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/29 10:00 | Daria Kudashova v Saar, Katriin | 6-3,6-3 |
| Batumi, Singles Qualifying W-ITF-GEO-02A | 2019/08/28 12:25 | Daria Kudashova v Bursa, Anastasia | 7-5,6-2 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/08/04 08:30 | Anna Turati v Daria Kudashova | 6-0,6-3 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/08/03 08:30 | Daria Kudashova v Eva Vedder | 0-6,7-5,6-3 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/08/02 10:00 | Daria Kudashova v Lantigua de La Nuez, Ana | 6-4,6-3 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/08/01 08:00 | Daria Kudashova v Bertoloni, Anita | 6-4,6-2 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/07/30 09:05 | Daria Kudashova v Baravi, Adelina | 6-0,6-0 |