Round: 25 Ground: Hardcourt outdoor
| Challenger Istanbul Qual | 2016/09/11 09:00 | Kimmer Coppejans v Kozyukov, Vitaly | 6-2,3-6,4-6 |
| Challenger Istanbul Qual | 2016/09/10 10:35 | Mustafa Erdogan v Kozyukov, Vitaly | 3-6,1-6 |
| ITF Russia F8 | 2016/09/07 10:10 | Alexander Vasilenko v Kozyukov, Vitaly | 7-6,6-3 |
| ITF Russia F8 | 2016/09/06 11:00 | Kozyukov, Vitaly v Ayap, Sagadat | 6-3,5-7,6-4 |
| ITF Russia F7 | 2016/08/31 12:30 | Alexander Bublik v Kozyukov, Vitaly | 6-3,6-4 |
| ITF Russia F7 | 2016/08/29 09:15 | Khomich, Aleksei v Kozyukov, Vitaly | 4-6,6-4,2-6 |
| ITF Russia F6 | 2016/08/19 07:00 | Kozyukov, Vitaly v Evgeny Karlovskiy | 3-6,2-6 |
| ITF Russia F6 | 2016/08/18 07:00 | Kozyukov, Vitaly v Sabanin, Yan | 6-2,3-6,6-4 |
| US Open 2016 | 2016/08/31 21:35 | Lucas Pouille v Chiudinelli, Marco | 4-6,3-6,7-6,6-2,6-0 |
| US Open, New York, USA | 2016/08/29 18:55 | Clezar, Guilherme v Chiudinelli, Marco | 6-2,6-7,2-6,4-6 |
| US Open, New York, USA, Qualifying | 2016/08/26 17:00 | Jozef Kovalik v Chiudinelli, Marco | 6-7,5-7 |
| US Open, New York, USA, Qualifying | 2016/08/25 15:00 | Tristan Lamasine v Chiudinelli, Marco | 4-6,6-3,6-7 |
| US Open, New York, USA, Qualifying | 2016/08/23 18:10 | Blaz Rola v Chiudinelli, Marco | 7-6,2-6,3-6 |
| Segovia, Spain | 2016/07/25 16:00 | Chiudinelli, Marco v Akira Santillan | 6-4,4-6,3-6 |
| Newport, USA | 2016/07/15 15:00 | Chiudinelli, Marco v Karlovic, Ivo | 3-6,4-6 |
| Newport, USA | 2016/07/13 16:30 | Chiudinelli, Marco v Smith, John-Patrick | 1-6,6-3,6-3 |