Stadium: Court 5 Round: 28 Ground: Clay
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/23 08:00 | Nikita Mashtakov v Vladyslav Orlov | 4-6,2-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/22 08:40 | Vladyslav Orlov v Jordan Correia Passos Do Carmo | 0-6,6-4,6-4 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/21 07:00 | Vladyslav Orlov v Shcherba, Vitalii | 6-4,3-6,7-6 |
| ITF - M15 Antalya | 2019/05/10 07:45 | Aleksandre Metreveli v Vladyslav Orlov | 3-6,6-4,7-5 |
| ITF - M15 Antalya | 2019/05/09 07:15 | Vladyslav Orlov v Luca Castelnuovo | 6-2,7-5 |
| ITF - M15 Antalya | 2019/05/08 13:00 | Bosnjak, Mislav v Vladyslav Orlov | 4-6,1-6 |
| ITF - M15 Antalya | 2019/05/04 07:45 | Vladyslav Orlov v Ergi Kirkin | 4-6,1-6 |
| ITF - M15 Antalya | 2019/05/02 07:15 | Vladyslav Orlov v Luca Castelnuovo | 6-0,6-4 |
| 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 |
| ITF Ukraine F4 | 2018/08/29 11:45 | Petit, Gabriel v Dolgosheyev, Oleg | 7-6,2-6,3-6 |
| ITF Ukraine F4 | 2018/08/27 08:30 | Parshutin, Denis v Dolgosheyev, Oleg | 3-6,7-5,3-6 |
| ITF Ukraine F3 | 2018/05/24 09:50 | Karimov, Jurabek v Dolgosheyev, Oleg | 6-1,7-5 |
| ITF Ukraine F3 | 2018/05/23 09:30 | Lebedyn, Alexander v Dolgosheyev, Oleg | 4-6,4-6 |
| ITF Ukraine F3 | 2018/05/22 10:45 | Dolgosheyev, Oleg v Katic, Dejan | 6-4,6-3 |