Round: 23 Ground: Hardcourt outdoor
| US Open Qual | 2016/08/26 15:00 | Guilherme Clezar v Alexander Sarkissian | 6-4,7-6 |
| US Open Qual | 2016/08/25 17:00 | Tim Smyczek v Guilherme Clezar | 6-7,3-6 |
| US Open Qual | 2016/08/23 19:20 | Facundo Arguello v Guilherme Clezar | 2-6,3-6 |
| Challenger Granby | 2016/08/03 16:00 | Mitchell Krueger v Guilherme Clezar | 6-4,7-6 |
| Wimbledon Qual | 2016/06/21 09:30 | Radu Albot v Guilherme Clezar | 6-3,6-3 |
| Challenger Blois | 2016/06/15 14:10 | Guilherme Clezar v Antal Van Der Duim | 1-6,4-6 |
| Challenger Blois | 2016/06/14 08:00 | Albert Montanes v Guilherme Clezar | 6-4,6-7,4-6 |
| Challenger Caltanissetta | 2016/06/07 12:10 | Guilherme Clezar v Gianluigi Quinzi | 2-6,6-1,6-7 |
| US Open Qual | 2016/08/26 17:00 | Jozef Kovalik 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 |
| Wimbledon Qual | 2016/06/21 11:10 | Alexander Kudryavtsev v Marco Chiudinelli | 7-5,3-6,6-3 |
| French Open Qual | 2016/05/16 11:10 | Marco Chiudinelli v Laslo Djere | 4-6,0-6 |