Stadium: Court 6 Round: 26 Ground: Clay
| ITF Ukraine F4 | 2018/08/30 07:00 | Oleg Dolgosheyev v Dmytro Kamynin | 6-0,3-6,1-6 |
| ITF M15 Irpin | 2019/05/21 08:55 | Oleg Dolgosheyev v Peter Goldsteiner | 4-6,6-1,6-3 |
| ITF Ukraine F4 | 2018/08/30 07:00 | Oleg Dolgosheyev v Dmytro Kamynin | 6-0,3-6,1-6 |
| ITF Ukraine F4 | 2018/08/29 11:45 | Gabriel Petit v Oleg Dolgosheyev | 7-6,2-6,3-6 |
| ITF Ukraine F4 | 2018/08/27 08:30 | Denis Parshutin v Oleg Dolgosheyev | 3-6,7-5,3-6 |
| ITF Ukraine F3 | 2018/05/24 09:50 | Jurabek Karimov v Oleg Dolgosheyev | 6-1,7-5 |
| ITF Ukraine F3 | 2018/05/23 09:30 | Alexander Lebedyn v Oleg Dolgosheyev | 4-6,4-6 |
| ITF Ukraine F3 | 2018/05/22 10:45 | Oleg Dolgosheyev v Dejan Katic | 6-4,6-3 |
| ITF Ukraine F2 | 2018/05/19 07:00 | Oleg Dolgosheyev v Jonas Merckx | 4-6,2-6 |
| ITF M15 Irpin | 2019/05/21 15:35 | Dmytro Kamynin v Daniel Michalski | 6-2,0-6,7-6 |
| ITF M15 Irpin | 2019/05/20 08:30 | Daniil Tsebrenko v Dmytro Kamynin | 2-6,2-6 |
| ITF M15 Irpin | 2019/05/20 07:00 | Sagadat Ayap v Dmytro Kamynin | 4-6,3-6 |
| ITF Ukraine F4 | 2018/08/31 08:00 | Oleksii Krutykh v Dmytro Kamynin | 7-6,6-2 |
| ITF Ukraine F4 | 2018/08/30 07:00 | Oleg Dolgosheyev v Dmytro Kamynin | 6-0,3-6,1-6 |
| ITF Ukraine F4 | 2018/08/29 11:20 | Dmytro Kamynin v Olexiy Kolisnyk | 6-4,7-5 |
| ITF Ukraine F3 | 2018/05/24 08:35 | Oleksii Krutykh v Dmytro Kamynin | 6-4,6-4 |
| ITF Ukraine F3 | 2018/05/23 11:00 | Dmytro Kamynin v Kristian Lozan | 7-6,0-6,6-2 |