Round: 44 Ground: Clay
| ITF M25 Irpin | 2019/08/26 07:30 | Oleg Dolgosheyev v Artur Kulibaba | 7-5,6-4 |
| ITF M15 Irpin | 2019/08/14 07:30 | Oleg Dolgosheyev v Nikita Mashtakov | 7-6,1-6,3-6 |
| ITF M15 Irpin | 2019/08/13 06:30 | Oleg Dolgosheyev v Ivan Liutarevich | 5-7,6-4,6-2 |
| ITF M15 Irpin | 2019/05/29 07:00 | Yan Bondarevskiy v Oleg Dolgosheyev | 7-5,6-3 |
| ITF M15 Irpin | 2019/05/28 10:15 | Andrii Gryniuk v Oleg Dolgosheyev | 2-6,1-6 |
| ITF M15 Irpin | 2019/05/24 08:00 | Vladyslav Orlov v Oleg Dolgosheyev | 6-1,6-1 |
| ITF M15 Irpin | 2019/05/23 08:00 | Tomas Liska v Oleg Dolgosheyev | 6-1,6-7,2-6 |
| ITF M15 Irpin | 2019/05/21 08:55 | Oleg Dolgosheyev v Peter Goldsteiner | 4-6,6-1,6-3 |
| ITF M25 Irpin | 2019/08/26 07:30 | Svyatoslav Ilnytskyy v Volodymyr Uzhylovskyi | 6-7,7-6,4-10 |
| ITF M25 Irpin | 2019/08/25 07:30 | Volodymyr Uzhylovskyi v Nikolay Vylegzhanin | 6-7,6-4,10-6 |
| Challenger Aptos | 2019/08/05 17:25 | Bernardo Saraiva v Volodymyr Uzhylovskyi | 2-6,3-6 |
| Challenger Binghamton | 2019/07/23 15:30 | Volodymyr Uzhylovskyi v Raymond Sarmiento | 3-6,6-3,2-6 |
| ITF M25 Iowa City | 2019/07/17 21:30 | Volodymyr Uzhylovskyi v Sumit Sarkar | 3-6,1-6 |
| ITF M25 Iowa City | 2019/07/16 16:55 | Volodymyr Uzhylovskyi v Sean Sculley | 6-4,6-4 |
| ITF M25 Iowa City | 2019/07/15 15:00 | Ronan Jachuck v Volodymyr Uzhylovskyi | 5-7,6-4,1-10 |
| Challenger Winnetka | 2019/07/08 15:00 | John McNally v Volodymyr Uzhylovskyi | 6-3,6-2 |