Round: 54 Ground: Clay
| ITF Russia F3 Qual | 2016/07/04 07:00 | Vladimir Polyakov v Andrey Chepelev | 4-6,6-2,6-4 |
| ITF Russia F5 Qual | 2016/08/07 08:30 | Andrey Chepelev v Sergei Pogosian | 6-3,6-4 |
| ITF Russia F4 Qual | 2016/07/31 07:00 | Maksim Mokrousov v Andrey Chepelev | 0-6,3-6 |
| ITF Spain F21 Qual | 2016/07/10 08:00 | Quim Sorni Chavarria v Andrey Chepelev | 5-7,3-6 |
| ITF Russia F3 Qual | 2016/07/04 07:00 | Vladimir Polyakov v Andrey Chepelev | 4-6,6-2,6-4 |
| ITF Russia F3 Qual | 2016/07/03 07:00 | Andrey Chepelev v Ilya Vasilyev | 3-6,6-3,6-4 |
| ITF Russia F3 Qual | 2016/07/02 09:00 | Andrey Chepelev v Ruslan Mugtasimov | 6-4,6-2 |
| ITF Russia F2 Qual | 2016/06/27 07:00 | Andrey Chepelev v Alexandr Semenov | 6-2,5-7,5-7 |
| ITF Russia F2 Qual | 2016/06/26 07:00 | Alexander Ovcharov v Andrey Chepelev | 5-7,2-6 |
| ITF Russia F4 | 2016/08/02 07:00 | Dmitry Surchenko v Vladimir Polyakov | 7-6,5-7,5-7 |
| ITF Estonia F1 | 2016/07/25 22:00 | Nicolas Alberto Arreche v Vladimir Polyakov | 7-6,6-2 |
| ITF Estonia F1 | 2016/07/23 22:00 | Vladimir Polyakov v Max Colorado | 6-3,6-3 |
| ITF Russia F3 | 2016/07/05 07:00 | Ivan Davydov v Vladimir Polyakov | 6-4,6-4 |
| ITF Russia F3 Qual | 2016/07/04 07:00 | Vladimir Polyakov v Andrey Chepelev | 4-6,6-2,6-4 |
| ITF Russia F3 Qual | 2016/07/03 07:00 | Vladimir Polyakov v Ivan Kalinin | 6-4,6-1 |
| ITF Russia F2 Qual | 2016/06/27 07:00 | Vladimir Korolev v Vladimir Polyakov | 6-3,4-6,7-5 |
| ITF Russia F2 Qual | 2016/06/26 07:00 | Kirill Komarov v Vladimir Polyakov | 6-3,2-6,4-6 |