Stadium: Court 6 Round: 25 Ground: Clay
| ITF Ukraine F2 | 2015/05/17 09:00 | Ivan Liutarevich v Dolgosheyev, Oleg | 3-6,4-6 |
| 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 |
| ITF Ukraine F4 | 2018/08/27 08:30 | Parshutin, Denis v Dolgosheyev, Oleg | 3-6,7-5,3-6 |
| ITF M15 Telavi | 2019/07/23 07:55 | Nikita Mashtakov v Ivan Liutarevich | 7-6,6-2 |
| Yinchuan, Simples M-ITF-CHN-11A | 2019/06/28 07:15 | Niki, Takuto v Ivan Liutarevich | 7-6,7-5 |
| Yinchuan, Simples M-ITF-CHN-11A | 2019/06/28 03:05 | Ivan Liutarevich v Wang, Ruixuan | 6-2,6-4 |
| Namangan, Singles Qualifying M-ITF-UZB-02A | 2019/05/02 08:05 | Ivan Liutarevich v Tyurnev, Evgeny | 2-6,4-6 |
| Namangan, Singles Qualifying M-ITF-UZB-02A | 2019/05/01 06:50 | Ivan Liutarevich v Ivan Denisov | 5-7,7-6,6-2 |
| Namangan, Singles Qualifying M-ITF-UZB-02A | 2019/04/30 09:15 | Ivan Liutarevich v Kumthonkittikul, W. | 6-4,6-4 |
| Namangan, Singles Qualifying M-ITF-UZB-02A | 2019/04/29 09:05 | Ivan Liutarevich v Korobeynikov, Grigoriy | 6-3,5-7,18-16 |
| Andijan, Singles Qualifying M-ITF-UZB-01A | 2019/04/24 06:50 | Takeuchi, Kento (1987) v Ivan Liutarevich | 6-3,3-6,6-4 |