Round: 25 Ground: Clay
| Challenger Todi | 2016/07/08 16:00 | Alessandro Giannessi v Marco Cecchinato | 4-6,6-2,3-6 |
| Challenger Todi | 2016/07/07 12:00 | Alessandro Giannessi v de Greef, Arthur | 4-6,6-0,6-1 |
| Challenger Todi | 2016/07/05 09:00 | Alessandro Giannessi v Steven Diez | 5-7,7-5,6-1 |
| Wimbledon Qual | 2016/06/21 11:20 | Salisbury, Joe v Alessandro Giannessi | 4-6,7-6,6-3 |
| Challenger - Perugia | 2016/06/15 09:00 | Nicolas Kicker v Alessandro Giannessi | 6-2,6-0 |
| Challenger Caltanissetta | 2016/06/11 15:30 | Lorenzi, Paolo v Alessandro Giannessi | 6-4,7-5 |
| Challenger Caltanissetta | 2016/06/10 13:00 | Alessandro Giannessi v Arevalo-Gonzalez, Marcelo | 6-4,6-1 |
| Challenger Caltanissetta | 2016/06/09 11:00 | Elias Ymer v Alessandro Giannessi | 4-6,4-6 |
| ITF Italy F19 | 2016/07/08 13:30 | Lipovsek Puches, Tomas v Juan Pablo Paz | 3-6,6-4,2-6 |
| ITF Italy F19 | 2016/07/07 13:20 | Lipovsek Puches, Tomas v Granollers, Gerard | 6-3,6-2 |
| ITF Italy F19 | 2016/07/06 18:00 | Lipovsek Puches, Tomas v Orlando Luz | 6-3,7-5 |
| ITF Italy F19 | 2016/07/05 08:00 | Lipovsek Puches, Tomas v Rizzuti, Giovanni | 7-5,6-3 |
| ITF France F12 | 2016/06/29 11:40 | Pedro Martinez v Lipovsek Puches, Tomas | 7-6,6-2 |
| ITF France F12 | 2016/06/27 09:00 | Mora, Maxime v Lipovsek Puches, Tomas | 6-1,2-6,2-6 |
| Wimbledon Qual | 2016/06/21 11:55 | Mohamed Safwat v Lipovsek Puches, Tomas | 6-3,6-2 |
| Challenger Poprad Tatry | 2016/06/14 08:00 | Norbert Gombos v Lipovsek Puches, Tomas | 6-2,6-4 |