Round: 25 Ground: Clay
| ITF Russia F8 Qual | 2016/09/04 08:50 | Alexander Ovcharov v Dmitry Mnushkin | 6-4,6-2 |
| ITF Russia F7 | 2016/08/30 09:50 | Marat Deviatiarov v Alexander Ovcharov | 6-7,7-6,6-3 |
| ITF Russia F7 Qual | 2016/08/28 07:00 | Egor Gerasimov v Alexander Ovcharov | 4-6,3-6 |
| ITF Russia F6 | 2016/08/19 07:00 | Alexander Ovcharov v R. Urzua-Rivera | 3-6,0-6 |
| ITF Russia F6 | 2016/08/18 07:00 | Shalva Dzhanashia v Alexander Ovcharov | 6-4,3-6,5-7 |
| ITF Russia F6 | 2016/08/16 07:00 | Timur Kiyamov v Alexander Ovcharov | 3-6,5-7 |
| ITF Russia F6 Qual | 2016/08/15 10:30 | Alexander Ovcharov v Oleksandr Bielinskyi | 6-1,6-0 |
| ITF Russia F5 | 2016/08/10 08:45 | Alexander Ovcharov v Richard Muzaev | 3-6,3-6 |
| ITF Russia F7 | 2016/08/31 08:00 | Vasko Mladenov v Alexey Vatutin | 1-6,2-6 |
| ITF Russia F7 | 2016/08/30 12:00 | Vasko Mladenov v Denis Matsukevich | 6-4,6-2 |
| ITF Belarus F1 | 2016/08/12 07:00 | Vasko Mladenov v Yaraslav Shyla | 6-7,2-6 |
| ITF Belarus F1 | 2016/08/11 13:00 | Vasko Mladenov v Marat Deviatiarov | 4-6,6-2,6-3 |
| ITF Belarus F1 | 2016/08/10 08:30 | Vasko Mladenov v Alon Elia | 6-4,7-5 |
| ITF Belarus 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 |