Round: 28 Ground: Clay
| Challenger Caltanissetta | 2016/06/10 17:00 | Paolo Lorenzi v Gonzalo Lama | 6-2,6-4 |
| Challenger Caltanissetta | 2016/06/09 15:00 | Paolo Lorenzi v Laslo Djere | 4-6,7-6,6-3 |
| Challenger Caltanissetta | 2016/06/07 19:40 | Paolo Lorenzi v Frederico Ferreira Silva | 7-6,6-4 |
| French Open | 2016/05/24 15:20 | Paolo Lorenzi v Carlos Berlocq | 3-6,0-6,2-6 |
| Challenger Mestre | 2016/05/21 13:00 | Paolo Lorenzi v Gastao Elias | 7-5,2-6,2-6 |
| Challenger Mestre | 2016/05/20 13:15 | Paolo Lorenzi v Dennis Novak | 2-6,6-4,6-4 |
| Challenger Mestre | 2016/05/19 09:00 | Paolo Lorenzi v Nicolas Jarry | 3-6,6-3,6-2 |
| Challenger Mestre | 2016/05/17 15:25 | Paolo Lorenzi v Bastian Trinker | 1-6,6-1,7-5 |
| Challenger Caltanissetta | 2016/06/10 13:00 | Alessandro Giannessi v Marcelo Arevalo | 6-4,6-1 |
| Challenger Caltanissetta | 2016/06/09 11:00 | Elias Ymer v Alessandro Giannessi | 4-6,4-6 |
| Challenger Caltanissetta | 2016/06/07 09:30 | Nicolas Jarry v Alessandro Giannessi | 6-4,5-7,4-6 |
| French Open Qual | 2016/05/16 14:30 | Alessandro Giannessi v Ryan Harrison | 3-6,2-6 |
| Challenger Santiago 2 Qual | 2016/03/10 21:00 | Alessandro Giannessi v Gonzalo Lama | 7-5,2-6,6-7 |
| Challenger Santiago 2 Qual | 2016/03/08 19:45 | Alessandro Giannessi v Christian Lindell | 7-6,7-5 |
| Challenger Morelos | 2016/02/19 17:00 | Alessandro Giannessi v Alejandro Gonzalez | 3-6,1-6 |
| Challenger Morelos | 2016/02/18 19:30 | Alessandro Giannessi v Alexander Sarkissian | 2-6,6-1,6-3 |