Round: 25 Ground: Clay
| ITF - Weißrussland F1 | 2016/08/12 07:00 | Vasko Mladenov v Yaraslav Shyla | 6-7,2-6 |
| ITF - Weißrussland F1 | 2016/08/11 13:00 | Vasko Mladenov v Marat Deviatiarov | 4-6,6-2,6-3 |
| ITF - Weißrussland F1 | 2016/08/10 08:30 | Vasko Mladenov v Alon Elia | 6-4,7-5 |
| ITF - Weißrussland F1 | 2016/08/08 11:40 | Vasko Mladenov v Alexander Lebedyn | 6-7,7-6,6-2 |
| Davis Cup | 2016/07/17 09:00 | Moez Echargui v Vasko Mladenov | 7-6,5-7,6-7 |
| ITF - Ukraine F3 | 2016/05/24 12:20 | Vladyslav Manafov v Vasko Mladenov | 6-3,6-4 |
| ITF - Ukraine F2 | 2016/05/18 08:00 | Vladimir Ivanov v Vasko Mladenov | 6-3,6-2 |
| ITF - Ukraine F1 | 2016/05/10 08:25 | Sander Gille v Vasko Mladenov | 6-4,7-5 |
| ITF - Russland F6 | 2016/08/21 07:00 | Ivan Gakhov v Denis Matsukevich | 1-6,6-3,6-3 |
| ITF - Russland F6 | 2016/08/20 09:30 | Denis Matsukevich v Evgeny Karlovskiy | 3-6,7-6,7-5 |
| ITF - Russland F6 | 2016/08/19 07:00 | Alexander Igoshin v Denis Matsukevich | 4-6,5-7 |
| ITF - Russland F6 | 2016/08/18 07:00 | Denis Matsukevich v Elmar Ejupovic | 6-4,1-6,6-3 |
| ITF - Russland F6 | 2016/08/16 10:10 | Denis Matsukevich v Pavel Kotov | 6-4,2-6,7-5 |
| ITF - Russland F5 | 2016/08/09 07:00 | Timur Kiyamov v Denis Matsukevich | 7-6,4-6,6-3 |
| ITF - Russland F4 | 2016/08/03 07:00 | Alexander Igoshin v Denis Matsukevich | 7-6,6-3 |
| ITF - Russland F4 | 2016/08/01 07:00 | Denis Matsukevich v Oleg Ladik | 6-1,6-0 |