Stadium: Court 7 Round: 26 Ground: Clay
| ITF Ukraine F3 | 2015/05/23 07:00 | Dolgosheyev, Oleg v Nikita Mashtakov | 4-6,6-3,3-6 |
| 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 |
| ITF Ukraine F4 | 2018/08/29 11:45 | Petit, Gabriel v Dolgosheyev, Oleg | 7-6,2-6,3-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/08/13 08:50 | Kamynin, Dmytro v Nikita Mashtakov | 6-7,7-5,2-6 |
| ITF M15 Telavi | 2019/08/01 07:40 | Alexander Donski v Nikita Mashtakov | 7-6,6-0 |
| ITF M15 Telavi | 2019/07/30 06:45 | Nikita Mashtakov v Davlianidze, Nikoloz | 6-3,7-5 |
| ITF M15 Telavi | 2019/07/28 12:00 | Uspensky, Dennis v Nikita Mashtakov | 3-6,4-6 |
| ITF M15 Telavi | 2019/07/26 06:00 | Nikita Mashtakov v Tsivadze, George | 6-3,6-4 |
| ITF M15 Telavi | 2019/07/25 09:15 | Bondarevskiy, Yan v Nikita Mashtakov | 6-1,2-6,5-7 |
| ITF M15 Telavi | 2019/07/23 07:55 | Nikita Mashtakov v Ivan Liutarevich | 7-6,6-2 |
| ITF M15 Parnu | 2019/07/20 09:45 | Zopp, Jurgen v Nikita Mashtakov | 6-3,6-4 |