Round: 25 Ground: Clay
| Challenger Rome 2 Qual | 2016/09/24 10:00 | Daniele Spinnato v Alessandro Cortegiani | 6-3,6-2 |
| ITF Morocco F5 | 2016/07/30 22:00 | Alessandro Cortegiani v Hugo Pontico | 3-6,0-6 |
| ITF Morocco F4 | 2016/07/25 09:00 | Alessandro Cortegiani v Aaron Cortes Alcaraz | 5-7,7-6,2-6 |
| Challenger San Benedetto Qual | 2016/07/09 13:40 | Michael Linzer v Alessandro Cortegiani | 6-2,6-0 |
| ITF Italy F19 | 2016/07/03 08:50 | Alessandro Cortegiani v Alessandro Ceppellini | 1-6,6-4,1-6 |
| ITF Italy F19 | 2016/07/02 13:10 | Alessandro Cortegiani v Jesse Ross | 6-4,6-2 |
| ITF Italy F18 Qual | 2016/06/26 10:00 | Luca Tomasetto v Alessandro Cortegiani | 6-1,2-6,7-5 |
| ITF Italy F18 Qual | 2016/06/25 10:00 | Nicolo Inserra v Alessandro Cortegiani | 4-6,1-6 |
| ITF Italy F35 Qual | 2016/10/23 07:30 | Luca Prevosto v Juan Ignacio Iliev | 6-4,6-2 |
| ITF Italy F34 | 2016/10/18 08:30 | Luca Prevosto v Maxime Chazal | 2-6,1-6 |
| ITF Italy F31 | 2016/09/27 09:45 | Luca Prevosto v Francesco Picco | 4-6,2-6 |
| ITF Italy F31 Qual | 2016/09/25 07:30 | Alessio Giannuzzi v Luca Prevosto | 5-7,2-6 |
| ITF Italy F31 Qual | 2016/09/24 07:30 | Marco Miceli v Luca Prevosto | 2-6,4-6 |
| ITF Italy F30 | 2016/09/18 07:30 | Alessio Giannuzzi v Luca Prevosto | 6-0,6-1 |
| ITF Italy F29 | 2016/09/12 11:45 | Andrea Vavassori v Luca Prevosto | 6-3,6-4 |
| Challenger Genova Qual | 2016/09/04 15:45 | Danilo Petrovic v Luca Prevosto | 6-3,6-2 |