Round: 44 Ground: Carpet indoor
| 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 Russia F7 Qual | 2016/08/27 09:00 | Khomentovskiy, Matvey v Yatsik, Yahor | 6-1,0-6,6-2 |
| ITF Finland F3 | 2016/08/15 22:00 | Khomentovskiy, Matvey v Makiguchi, Ryusei | 4-6,0-6 |
| ITF Ukraine F5 | 2016/09/25 07:00 | Oleksii Krutykh v Kokulewski, Arnold | 6-3,6-0 |
| ITF Ukraine F4 Qual | 2016/09/19 08:40 | Yastremskiy, Simon v Kokulewski, Arnold | 7-5,6-2 |
| ITF Ukraine F4 Qual | 2016/09/18 07:00 | Kokulewski, Arnold v Egor Matvievici | 6-4,6-1 |
| ITF Ukraine F4 Qual | 2016/09/17 07:00 | Yehorov, Vasil v Kokulewski, Arnold | 2-6,6-4,2-6 |
| ITF Poland F6 Qual | 2016/08/21 11:00 | Krstev, Ondrej v Kokulewski, Arnold | 6-2,6-1 |
| ITF Czech Republic F1 Qual | 2016/05/08 08:00 | Kokulewski, Arnold v Grund, Gil Uwe | 4-6,4-6 |
| ITF USA F16 | 2016/04/29 12:30 | Boggs, Brian v Kokulewski, Arnold | 4-6,6-4,2-6 |
| ITF Greece F8 | 2015/10/17 08:30 | Kokulewski, Arnold v Raul Brancaccio | 2-6,0-6 |