Round: 26 Ground: Clay
| ITF Kazakhstan F8 | 2014/08/05 06:40 | Denis Matsukevich v Dzmitry Zhyrmont | 4-6,6-3,0-6 |
| ITF Russia F8 | 2016/09/05 10:05 | Dzmitry Zhyrmont v Maxim Kravtsov | 6-4,6-2 |
| ITF Russia F7 | 2016/08/31 10:00 | Dzmitry Zhyrmont v Marat Deviatiarov | 4-6,6-4,2-6 |
| ITF Russia F7 | 2016/08/30 08:00 | Dzmitry Zhyrmont v Nikita Mishin | 3-6,6-1,6-4 |
| ITF Belarus F1 | 2016/08/13 08:00 | Dzmitry Zhyrmont v Yaraslav Shyla | 4-6,1-6 |
| ITF Belarus F1 | 2016/08/12 07:00 | Dzmitry Zhyrmont v Artur Dubinski | 6-1,6-1 |
| ITF Belarus F1 | 2016/08/11 13:00 | Dzmitry Zhyrmont v Roman Khassanov | 6-0,6-1 |
| ITF Belarus F1 | 2016/08/10 07:00 | Dzmitry Zhyrmont v Szymon Walkow | 6-1,6-1 |
| ITF Belarus F1 | 2016/08/08 10:05 | Dzmitry Zhyrmont v Denis Yevseyev | 6-3,2-6,6-4 |
| ITF Russia F7 | 2016/08/30 12:00 | Vasko Mladenov v Denis Matsukevich | 6-4,6-2 |
| ITF Russia F6 | 2016/08/21 07:00 | Ivan Gakhov v Denis Matsukevich | 1-6,6-3,6-3 |
| ITF Russia F6 | 2016/08/20 09:30 | Denis Matsukevich v Evgeny Karlovskiy | 3-6,7-6,7-5 |
| ITF Russia F6 | 2016/08/19 07:00 | Alexander Igoshin v Denis Matsukevich | 4-6,5-7 |
| ITF Russia F6 | 2016/08/18 07:00 | Denis Matsukevich v Elmar Ejupovic | 6-4,1-6,6-3 |
| ITF Russia F6 | 2016/08/16 10:10 | Denis Matsukevich v Pavel Kotov | 6-4,2-6,7-5 |
| ITF Russia F5 | 2016/08/09 07:00 | Timur Kiyamov v Denis Matsukevich | 7-6,4-6,6-3 |
| ITF Russia F4 | 2016/08/03 07:00 | Alexander Igoshin v Denis Matsukevich | 7-6,6-3 |