Round: 29 Ground: Clay
| Challenger Caltanissetta | 2016/06/11 15:30 | Paolo Lorenzi v Alessandro Giannessi | 6-4,7-5 |
| 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 Caltanissetta | 2016/06/11 13:00 | Guido Andreozzi v Matteo Donati | 6-4,5-7,2-6 |
| Challenger Caltanissetta | 2016/06/10 14:30 | Matteo Donati v Gianluigi Quinzi | 6-4,3-6,6-4 |
| Challenger Caltanissetta | 2016/06/08 17:20 | Santiago Giraldo v Matteo Donati | 2-6,6-3,6-7 |
| Challenger Caltanissetta | 2016/06/07 09:30 | Matteo Donati v Miljan Zekic | 6-3,5-7,7-6 |
| Challenger Vicenza | 2016/05/24 13:45 | Matteo Donati v Henri Laaksonen | 4-6,6-7 |
| French Open Qual | 2016/05/20 09:50 | Matteo Donati v Gerald Melzer | 4-6,4-6 |
| French Open Qual | 2016/05/18 13:45 | Elias Ymer v Matteo Donati | 2-6,6-2,5-7 |
| French Open Qual | 2016/05/17 08:00 | Matteo Donati v James Ward | 6-4,6-3 |