Stadium: Court 5 Round: 44 Ground: Clay
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/08/14 07:30 | Dolgosheyev, Oleg v Nikita Mashtakov | 7-6,1-6,3-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/08/13 06:30 | Dolgosheyev, Oleg v Ivan Liutarevich | 5-7,6-4,6-2 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/29 07:00 | Bondarevskiy, Yan v Dolgosheyev, Oleg | 7-5,6-3 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/28 10:15 | Gryniuk, Andrii v Dolgosheyev, Oleg | 2-6,1-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/24 08:00 | Vladyslav Orlov v Dolgosheyev, Oleg | 6-1,6-1 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/23 08:00 | Liska, Tomas v Dolgosheyev, Oleg | 6-1,6-7,2-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/21 08:55 | Dolgosheyev, Oleg v Goldsteiner, Peter | 4-6,6-1,6-3 |
| ITF Ukraine F4 | 2018/08/30 07:00 | Dolgosheyev, Oleg v Kamynin, Dmytro | 6-0,3-6,1-6 |
| Irpin, Singles Qualifying M-ITF-UKR-05A | 2019/08/25 07:30 | Kulibaba, Artur v Oswald, Jack | 6-4,6-4 |
| Minsk, Singles M-ITF-BLR-01A | 2019/08/20 07:00 | Beibit Zhukayev v Kulibaba, Artur | 6-1,6-2 |
| Minsk, Singles M-ITF-BLR-01A | 2019/08/19 10:50 | Kulibaba, Artur v Gurevich, Victor | 4-6,6-2,10-8 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/08/13 06:30 | Kulibaba, Artur v Maulenov, Timur | 2-6,6-2,2-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/07/29 07:30 | Arh, Anze v Kulibaba, Artur | 6-1,3-6,10-7 |
| ITF Estonia F2 | 2018/10/27 08:00 | Parts, Robin Erik v Kulibaba, Artur | 6-2,3-6,6-3 |
| ITF Turkey F31 | 2018/10/07 09:30 | Giuseppe La Vela v Kulibaba, Artur | 6-3,6-1 |
| ITF Turkey F31 | 2018/10/06 12:00 | Kulibaba, Artur v Leuch, Vital Flurin | 6-2,6-2 |