Round: 44 Ground: Clay
| ITF Ukraine F2 | 2016/05/15 07:00 | Boychuk, Roman v Nikita Mashtakov | 6-7,5-7 |
| ITF Ukraine F5 | 2016/09/24 09:30 | Vaise, Tomas v Boychuk, Roman | 6-7,2-6 |
| ITF Ukraine F4 Qual | 2016/09/19 08:40 | Boychuk, Roman v Dzhavakian, Yurii | 5-7,3-6 |
| Czech Republic F6, Singles Qualifying | 2016/07/09 13:00 | Boychuk, Roman v Stosic, Marko | 7-5,3-6,6-7 |
| ITF Ukraine F3 | 2016/05/22 07:00 | Boychuk, Roman v Resnyanskiy, Dmitry | 4-6,4-6 |
| ITF Ukraine F3 | 2016/05/21 07:00 | Boychuk, Roman v Sergiienko, Sergiy | 6-2,1-6,6-4 |
| ITF Ukraine F2 | 2016/05/15 07:00 | Boychuk, Roman v Nikita Mashtakov | 6-7,5-7 |
| ITF Ukraine F1 | 2016/05/07 07:30 | Boychuk, Roman v Veremeychuk, Danylo | 2-6,6-4,2-6 |
| ITF Egypt F4 | 2016/02/06 10:30 | Tsoronis, Socrates Leon v Boychuk, Roman | 3-6,6-3,6-3 |
| ITF Ukraine F5 | 2016/09/25 09:30 | Smolicki, Mateusz v Nikita Mashtakov | 3-6,4-6 |
| ITF Ukraine F4 | 2016/09/20 08:10 | Nikita Mashtakov v Alekseenko, Vadim | 4-6,4-6 |
| ITF Ukraine F2 | 2016/05/19 11:45 | Kamil Majchrzak v Nikita Mashtakov | 6-1,6-4 |
| ITF Ukraine F2 | 2016/05/18 10:00 | Alekseenko, Gleb v Nikita Mashtakov | 4-6,4-6 |
| ITF Ukraine F2 | 2016/05/15 07:00 | Boychuk, Roman v Nikita Mashtakov | 6-7,5-7 |
| ITF Ukraine F1 | 2016/05/10 07:00 | Galoppini, Davide v Nikita Mashtakov | 6-2,6-2 |
| ITF Ukraine F1 | 2016/05/09 07:00 | Georgii Kravchenko v Nikita Mashtakov | 5-7,1-6 |
| ITF Ukraine F1 | 2016/05/08 10:30 | Milchenko, Denis v Nikita Mashtakov | 6-2,5-7,3-6 |