Stadium: Court 1 Round: 26 Ground: Clay
| ITF W15 Prokuplje | 2019/07/03 07:00 | Yukina Saigo v Oleksandra Oliynykova | 1-6,3-6 |
| ITF W15 Budapest | 2019/06/26 08:00 | Oleksandra Oliynykova v Romana Cisovska | 6-3,2-6,2-6 |
| ITF - W15 Héraklion | 2019/06/02 07:00 | Oleksandra Oliynykova v Oana Gavrila | 1-6,3-6 |
| ITF - W15 Héraklion | 2019/06/01 09:40 | Oleksandra Oliynykova v Dalakishvili, Mariam | 7-6,7-6 |
| ITF - W15 Héraklion | 2019/05/31 07:00 | Malesevic, Tamara v Oleksandra Oliynykova | 6-2,2-6,4-6 |
| ITF - W15 Héraklion | 2019/05/30 07:00 | Chen, Pei Hsuan v Oleksandra Oliynykova | 3-6,4-6 |
| ITF - W15 Héraklion | 2019/05/29 12:05 | Poile, Miranda v Oleksandra Oliynykova | 1-6,4-6 |
| ITF - W15 Héraklion | 2019/05/24 07:00 | Oleksandra Oliynykova v Malesevic, Tamara | 2-6,2-6 |
| ITF W15 Prokuplje | 2019/07/03 13:20 | Takamura, Satsuki v Draginja Vukovic | 3-6,4-6 |
| ITF W25 Klosters | 2019/06/20 08:50 | Draginja Vukovic v Julia Grabher | 6-4,6-7,4-6 |
| ITF W25 Klosters | 2019/06/19 12:35 | Draginja Vukovic v Yana Morderger | 6-2,7-6 |
| ITF - W15 Banja Luka | 2019/06/08 09:00 | Draginja Vukovic v Milkova, Barbora | 6-2,3-6,3-6 |
| ITF - W15 Banja Luka | 2019/06/06 11:55 | Gemovic, Elena v Draginja Vukovic | 3-6,0-6 |
| ITF - W15 Banja Luka | 2019/06/06 07:00 | Lukic, Jelena v Draginja Vukovic | 2-6,1-6 |
| ITF - W15 Héraklion | 2019/05/15 11:15 | Draginja Vukovic v Nadel, Nicole | 5-7,6-4,3-6 |
| ITF - W15 Héraklion | 2019/05/11 07:30 | Harvison, Isabella v Draginja Vukovic | 2-6,3-6 |