Round: 44 Ground: Clay
| 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 F2 Qual | 2016/06/25 07:00 | Andrey Chepelev v Ivan Kalinin | 6-1,6-2 |
| ITF Russia F1 Qual | 2016/06/18 09:30 | Artur Shakhnubaryan v Andrey Chepelev | 6-4,7-5 |
| ITF Spain F15 Qual | 2016/05/23 13:00 | Pavel Krainik v Andrey Chepelev | 6-1,6-4 |
| ITF Spain F15 Qual | 2016/05/22 10:00 | Mikayel Khachatryan v Andrey Chepelev | 3-6,3-6 |
| ITF Spain F15 Qual | 2016/05/21 12:30 | Lofo Ramiaramanana v Andrey Chepelev | 5-7,4-6 |
| ITF Russia F2 | 2016/07/01 08:00 | Evgeny Karlovskiy v Ilya Vasilyev | 6-3,6-1 |
| ITF Russia F2 | 2016/06/28 09:25 | Ilya Vasilyev v Alexander Bublik | 3-6,7-6,6-3 |
| ITF Russia F1 | 2016/06/20 09:15 | Mikhail Sokolovskiy v Ilya Vasilyev | 6-2,3-6,6-2 |
| ITF Russia F1 Qual | 2016/06/19 07:00 | Mikhail Galyamov v Ilya Vasilyev | 2-6,6-4,3-6 |
| ITF Russia F1 Qual | 2016/06/18 09:30 | Maxim Geraskin v Ilya Vasilyev | 1-6,3-6 |
| ITF Bosnia and Herzegovina F3 Qual | 2016/05/22 11:00 | Rajko Mladenovic v Ilya Vasilyev | 6-3,3-6,7-5 |
| ITF Kazakhstan F4 | 2016/04/27 07:20 | Ilya Vasilyev v Artem Smirnov | 1-6,5-7 |
| ITF Kazakhstan F4 | 2016/04/26 10:05 | Pavel Tsoy v Ilya Vasilyev | 3-6,0-6 |