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