Round: 25 Ground: Carpet indoor
| ITF Germany F14 | 2016/10/10 10:00 | Khomentovskiy, Matvey v Born, Yannick Stephan | 3-6,6-3,7-6 |
| ITF Germany F14 | 2016/10/09 08:00 | Khomentovskiy, Matvey v Kokulewski, Arnold | 6-4,6-1 |
| ITF Germany F13 | 2016/10/04 07:30 | Khomentovskiy, Matvey v Karlo Cubelic | 2-6,4-6 |
| ITF Germany F13 | 2016/10/03 07:30 | Khomentovskiy, Matvey v Zick, Charly | 6-1,6-1 |
| ITF Russia F8 | 2016/09/06 11:10 | Sabanin, Yan v Khomentovskiy, Matvey | 6-3,3-6,6-3 |
| Russia F8, Singles Qualifying | 2016/09/04 07:00 | Khomentovskiy, Matvey v Boris Pokotilov | 4-6,6-2,6-3 |
| ITF Russia F7 | 2016/08/29 07:00 | Egor Gerasimov v Khomentovskiy, Matvey | 4-6,6-3,6-3 |
| ITF Russia F7 Qual | 2016/08/28 08:55 | Khomentovskiy, Matvey v Ayap, Sagadat | 6-2,6-4 |
| ITF Germany F13 | 2016/10/05 16:30 | Podzus, Martins v Louis Wessels | 4-6,6-4,6-4 |
| ITF Germany F12 | 2016/08/27 13:40 | Louis Wessels v Lazov, Alexander | 3-6,1-6 |
| ITF Germany F12 | 2016/08/26 12:00 | Louis Wessels v Lenz, Julian | 6-3,5-7,6-4 |
| ITF Germany F12 | 2016/08/25 12:25 | Louis Wessels v Schmid, Michal | 6-3,6-2 |
| ITF Germany F12 | 2016/08/24 08:00 | Louis Wessels v Peham, Robin | 6-4,6-2 |
| ITF Germany F11 | 2016/08/18 10:00 | Louis Wessels v Wagner, Bastian | 4-6,4-6 |
| ITF Germany F11 | 2016/08/16 09:30 | Louis Wessels v Wilson Leite | 4-6,6-3,6-2 |
| Hamburg, Germany | 2016/07/14 13:10 | Martin Klizan v Louis Wessels | 6-1,6-1 |