Stadium: Court 5 Round: 26 Ground: Clay
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/28 07:00 | Michael Zhu v Bondarevskiy, Yan | 3-6,2-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/21 10:00 | Denis Yevseyev v Bondarevskiy, Yan | 6-3,6-3 |
| Namangan, Singles Qualifying M-ITF-UZB-02A | 2019/04/30 13:30 | Bondarevskiy, Yan v Timofey Skatov | 6-2,1-6,4-6 |
| Andijan, Singles Qualifying M-ITF-UZB-01A | 2019/04/25 07:00 | Roman Safiullin v Bondarevskiy, Yan | 6-3,7-5 |
| Andijan, Singles Qualifying M-ITF-UZB-01A | 2019/04/23 05:00 | Bondarevskiy, Yan v Scott Duncan | 6-2,3-6,10-6 |
| Andijan, Singles Qualifying M-ITF-UZB-01A | 2019/04/22 05:00 | Bondarevskiy, Yan v Dadabaev, Aziz | 6-1,6-4 |
| Shymkent, Singles Qualifying M-ITF-KAZ-03A | 2019/04/17 07:25 | Boborykin, Alexander v Bondarevskiy, Yan | 2-6,7-6,6-3 |
| Shymkent, Singles Qualifying M-ITF-KAZ-03A | 2019/04/16 07:40 | Bondarevskiy, Yan v Shrolik, Igor | 6-2,6-3 |
| 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 Ukraine F3 | 2018/05/24 09:50 | Karimov, Jurabek v Dolgosheyev, Oleg | 6-1,7-5 |