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