Stadium: Court 5 Round: 26 Ground: Clay
| 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 |
| 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 |
| Telavi, Singles W-ITF-GEO-04A | 2019/10/15 08:55 | Joksovic, Doroteja v Anna Siskova | 4-6,3-6 |
| Telavi, Singles W-ITF-GEO-04A | 2019/10/13 07:00 | Oana Georgeta Simion v Anna Siskova | 6-2,6-3 |
| Telavi, Singles W-ITF-GEO-04A | 2019/10/12 08:00 | Astakhova, Darya v Anna Siskova | 3-6,6-3,5-7 |
| Telavi, Singles W-ITF-GEO-04A | 2019/10/11 07:40 | Vdovenco, Anastasia v Anna Siskova | 6-3,1-6,2-6 |
| Telavi, Singles W-ITF-GEO-04A | 2019/10/10 06:00 | Joksovic, Doroteja v Anna Siskova | 2-6,1-6 |
| Telavi, Singles W-ITF-GEO-04A | 2019/10/09 08:15 | Elizaveta Shebekina v Anna Siskova | 1-6,3-6 |
| Brno, Singles Qualifying W-ITF-CZE-11A | 2019/09/24 11:20 | Anna Siskova v Matvienko, Lisa | 2-6,6-4,4-6 |
| ITF W25 Frydek Mistek | 2019/09/13 10:00 | Anna Siskova v Gerlach, Katharina | 1-6,2-6 |