Round: 44 Ground: Clay
| ITF Germany F13 | 2016/10/03 07:30 | Matvey Khomentovskiy v Чарли Зик | 6-1,6-1 |
| ITF Russia F8 | 2016/09/06 11:10 | Ян Сабанин v Matvey Khomentovskiy | 6-3,3-6,6-3 |
| ITF Russia F8 Qual | 2016/09/04 07:00 | Matvey Khomentovskiy v Борис Покотилов | 4-6,6-2,6-3 |
| ITF Russia F7 | 2016/08/29 07:00 | Егор Герасимов v Matvey Khomentovskiy | 4-6,6-3,6-3 |
| ITF Russia F7 Qual | 2016/08/28 08:55 | Matvey Khomentovskiy v Sagadat Ayap | 6-2,6-4 |
| ITF Russia F7 Qual | 2016/08/27 09:00 | Matvey Khomentovskiy v Yahor Yatsyk | 6-1,0-6,6-2 |
| ITF Finland F3 | 2016/08/15 22:00 | Matvey Khomentovskiy v Ryusei Makiguchi | 4-6,0-6 |
| ITF Finland F3 Qual | 2016/08/13 22:00 | Matvey Khomentovskiy v Lorenzo Di Maro | 6-3,6-3 |
| ITF Netherlands F7 | 2016/08/27 08:00 | Карло Кубелик v Лион Ховлер | 4-6,4-6 |
| ITF Germany F8 Qual | 2016/07/18 10:00 | George Von Massow v Карло Кубелик | 6-1,6-4 |
| ITF Germany F8 Qual | 2016/07/17 08:30 | Карло Кубелик v Aljaz Jakob Kaplja | 6-3,7-5 |
| ITF Germany F1 Qual | 2016/01/11 08:00 | Fran Zvonimir Zgombic v Карло Кубелик | 6-3,6-3 |