Round: 25 Ground: Clay
| ITF Ukraine F2 | 2016/05/21 11:00 | Volodymyr Uzhylovskyi v Vladyslav Manafov | 4-6,6-3,4-6 |
| ITF Ukraine F2 | 2016/05/20 09:25 | Volodymyr Uzhylovskyi v Davide Galoppini | 6-2,7-5 |
| ITF Ukraine F2 | 2016/05/19 10:45 | Volodymyr Uzhylovskyi v Artur Dubinski | 4-6,6-4,6-3 |
| ITF Ukraine F2 | 2016/05/16 09:30 | Volodymyr Uzhylovskyi v Kristian Lozan | 1-6,6-2,6-0 |
| ITF Ukraine F1 | 2016/05/10 10:55 | Kristian Lozan v Volodymyr Uzhylovskyi | 5-7,7-6,6-3 |
| Challenger Rome Qual | 2016/04/30 12:55 | Ivan Nedelko v Volodymyr Uzhylovskyi | 6-2,6-4 |
| Challenger Rome Qual | 2016/04/30 10:10 | Volodymyr Uzhylovskyi v Gianmarco De Santis | 2-6,6-1,6-1 |
| ITF Israel F6 | 2016/03/20 08:30 | Volodymyr Uzhylovskyi v Yannai Barkai | 1-6,3-6 |
| ITF Ukraine F2 | 2016/05/15 08:00 | Vladyslav Orlov v Oleksander Kyrychenko | 4-6,1-6 |
| ITF Ukraine F1 | 2016/05/10 09:10 | Joran Vliegen v Vladyslav Orlov | 7-5,6-1 |
| ITF Ukraine F1 | 2016/05/09 06:30 | Vladyslav Orlov v Daniil Tsebrenko | 6-3,6-3 |
| ITF Egypt F12 | 2016/04/05 08:00 | Vladyslav Orlov v Tomas Papik | 0-6,2-6 |
| ITF Egypt F12 | 2016/04/04 08:00 | Vladyslav Orlov v Michal Kominek | 6-0,6-1 |
| ITF Egypt F3 | 2016/02/01 09:45 | Keelan Oakley v Vladyslav Orlov | 6-2,6-0 |
| ITF Egypt F3 | 2016/01/31 10:00 | Bogdan Didenko v Vladyslav Orlov | 7-6,3-6,2-6 |
| ITF Egypt F2 | 2016/01/25 08:00 | Oleg Khotkov v Vladyslav Orlov | 6-3,6-1 |