Stadium: Court 5 Round: 26 Ground: Clay
| ITF W15 - Chornomorsk | 2019/10/05 12:50 | Federica Arcidiacono v Valeriya Olyanovskaya | 6-3,4-6,7-6 |
| ITF W15 - Chornomorsk | 2019/10/04 13:10 | Valeriya Olyanovskaya v Yulia Zhytelna | 6-1,6-0 |
| ITF W15 - Chornomorsk | 2019/10/03 10:15 | Shelly Bereznyak v Valeriya Olyanovskaya | 6-7,1-6 |
| ITF W15 - Chornomorsk | 2019/10/01 08:55 | Anastasiya Klymenko v Valeriya Olyanovskaya | 1-6,1-6 |
| ITF W15 Batumi | 2019/08/31 08:45 | Valeriya Olyanovskaya v Daria Kudashova | 3-6,1-6 |
| ITF W15 Batumi | 2019/08/30 06:00 | Valeriya Olyanovskaya v Iveta Dapkute | 6-2,7-6 |
| ITF W15 Batumi | 2019/08/29 06:00 | Jacqueline Cabaj Awad v Valeriya Olyanovskaya | 4-6,6-1,1-6 |
| ITF W15 Batumi | 2019/08/28 09:30 | Tamari Gagoshidze v Valeriya Olyanovskaya | 3-6,1-6 |
| ITF W15 Telavi | 2019/10/15 08:55 | Doroteja Joksovic v Anna Siskova | 4-6,3-6 |
| ITF W15 Telavi | 2019/10/13 07:00 | Oana Georgeta Simion v Anna Siskova | 6-2,6-3 |
| ITF W15 Telavi | 2019/10/12 08:00 | Darya Astakhova v Anna Siskova | 3-6,6-3,5-7 |
| ITF W15 Telavi | 2019/10/11 07:40 | Anastasia Vdovenco v Anna Siskova | 6-3,1-6,2-6 |
| ITF W15 Telavi | 2019/10/10 06:00 | Doroteja Joksovic v Anna Siskova | 2-6,1-6 |
| ITF W15 Telavi | 2019/10/09 08:15 | Elizaveta Shebekina v Anna Siskova | 1-6,3-6 |
| ITF W25 Brno | 2019/09/24 11:20 | Anna Siskova v Lisa Matviyenko | 2-6,6-4,4-6 |
| ITF W25 - Frýdek-Místek | 2019/09/13 10:00 | Anna Siskova v Katharina Gerlach | 1-6,2-6 |