Stadium: Cancha 1 Round: 25 Ground: Clay
| Challenger Caltanissetta | 2016/06/07 12:10 | Guilherme Clezar v Gianluigi Quinzi | 2-6,6-1,6-7 |
| Challenger Las Vegas | 2016/10/17 19:30 | Guilherme Clezar v Marco Trungelliti | 6-3,4-6,4-6 |
| Challenger Monterrey | 2016/10/10 19:25 | Ruben Gonzales v Guilherme Clezar | 6-3,3-6,7-6 |
| Challenger Stockton | 2016/10/04 17:00 | Guilherme Clezar v Noah Rubin | 6-2,3-6,3-6 |
| Challenger Tiburon | 2016/09/26 22:00 | Stefan Kozlov v Guilherme Clezar | 6-2,6-2 |
| Challenger Columbus | 2016/09/21 15:50 | Guilherme Clezar v Frank Dancevic | 2-6,4-6 |
| 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 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 |
| Challenger Rome 2 | 2016/09/27 10:30 | Gianluigi Quinzi v Gianluca Mager | 3-6,5-7 |
| Challenger Genova | 2016/09/07 20:10 | Nicolas Almagro v Gianluigi Quinzi | 1-6,6-4,7-5 |
| Challenger Como | 2016/08/30 10:40 | Marco Trungelliti v Gianluigi Quinzi | 6-4,4-6,6-4 |
| Challenger Cortina | 2016/08/03 09:00 | Andrea Collarini v Gianluigi Quinzi | 7-6,7-6 |
| Challenger Cortina Qual | 2016/08/01 15:40 | Gianluigi Quinzi v Lucas Miedler | 7-6,5-7,6-2 |
| Challenger Cortina Qual | 2016/08/01 12:45 | Gianluigi Quinzi v Nicolo Turchetti | 6-3,6-2 |
| Challenger Biella | 2016/07/26 10:45 | Gianluigi Quinzi v Tomislav Brkic | 3-6,6-2,1-6 |
| Challenger San Benedetto | 2016/07/16 17:05 | Constant Lestienne v Gianluigi Quinzi | 7-6,6-4 |