Estádio: Clay 2 Round: 25 Ground: Clay
| ITF - W15 Heraklion | 2019/12/01 08:00 | Alina Mukhortova v Ema Bolebruchova | 6-0,6-3 |
| ITF - W15 Székesfehérvár | 2019/09/09 11:30 | Tina Cvetkovic v Ema Bolebruchova | 6-4,6-3 |
| ITF - W25 Praga | 2019/09/01 08:00 | Ema Bolebruchova v Ines Ibbou | 0-6,1-6 |
| ITF - W25 Bytom | 2019/07/23 09:05 | Daria Kuczer v Ema Bolebruchova | 6-4,6-4 |
| ITF - W25 Bytom | 2019/07/22 08:00 | Ema Bolebruchova v Juliane Triebe | 7-5,6-2 |
| ITF - W60 Stare Splavy | 2019/06/17 12:50 | Kamilla Rakhimova v Ema Bolebruchova | 6-0,6-4 |
| ITF - W15 Banja Luka | 2019/06/03 10:00 | Ema Bolebruchova v Iva Zelic | 3-6,0-6 |
| ITF Hua Hin - Feminino | 2018/12/04 04:05 | Ema Bolebruchova v Jessie Aney | 5-7,4-6 |
| ITF - W15 Heraklion | 2019/12/07 08:30 | Oleksandra Oliynykova v Claudia Hoste Ferrer | 7-6,6-7,2-6 |
| ITF - W15 Heraklion | 2019/12/06 08:00 | Oleksandra Oliynykova v Martina Spigarelli | 6-3,6-2 |
| ITF - W15 Heraklion | 2019/12/05 08:00 | Andrea Gamiz v Oleksandra Oliynykova | 3-6,2-6 |
| ITF - W15 Heraklion | 2019/12/03 09:30 | Eline Audenaert v Oleksandra Oliynykova | 3-6,2-6 |
| ITF - W15 Heraklion | 2019/11/30 10:20 | Noelia Zeballos v Oleksandra Oliynykova | 6-2,6-1 |
| ITF - W15 Heraklion | 2019/11/29 08:00 | Oleksandra Oliynykova v Celia Cervino Ruiz | 2-6,6-4,6-3 |
| ITF - W15 Heraklion | 2019/11/28 10:15 | Oleksandra Oliynykova v Laura Svatikova | 5-7,6-4,7-6 |
| ITF - W15 Heraklion | 2019/11/27 11:55 | Oleksandra Oliynykova v Anna Arkadianou | 7-6,7-5 |