Round: 25 Ground: Clay
| Challenger Casablanca Qual | 2016/10/09 11:30 | Danilo Petrovic v Marco Bortolotti | 6-1,6-0 |
| Challenger Casablanca Qual | 2016/10/08 15:45 | Ayoub Benamar v Marco Bortolotti | 4-6,1-6 |
| Challenger Rome 2 Qual | 2016/09/24 13:40 | Marco Bortolotti v Antonio Sancic | 6-4,2-6,4-6 |
| ITF Tunisia F24 | 2016/09/23 08:30 | Franco Agamenone v Marco Bortolotti | 6-4,1-6,6-4 |
| ITF Tunisia F24 | 2016/09/22 10:05 | Dimitriy Voronin v Marco Bortolotti | 3-6,1-6 |
| ITF Tunisia F24 | 2016/09/20 09:00 | Dante Gennaro v Marco Bortolotti | 4-6,5-7 |
| ITF Tunisia F24 | 2016/09/19 09:00 | Marco Bortolotti v Laerte Di Falco | 6-3,6-2 |
| ITF Tunisia F23 | 2016/09/18 09:00 | Marco Bortolotti v Mariano Kestelboim | 6-2,2-6,3-6 |
| ITF Italy F34 Qual | 2016/10/16 08:00 | Filippo Borella v Stefano Reitano | 7-6,3-6,1-6 |
| ITF Italy F34 Qual | 2016/10/15 08:00 | Ethan Tulliani v Stefano Reitano | 1-6,0-6 |
| ITF Italy F33 Qual | 2016/10/08 07:30 | Marco Miceli v Stefano Reitano | 6-3,5-7,7-6 |
| ITF Italy F32 Qual | 2016/10/02 07:30 | Alessandro Luisi v Stefano Reitano | 6-1,6-4 |
| ITF Italy F32 Qual | 2016/10/01 13:00 | Stefano Reitano v Flemming Peters | 7-6,6-1 |
| ITF Italy F31 Qual | 2016/09/25 07:30 | Stefano Reitano v Jacopo Berrettini | 7-6,4-6,2-6 |
| ITF Italy F31 Qual | 2016/09/24 07:30 | Loic Perret v Stefano Reitano | 6-3,1-6,4-6 |
| ITF Italy F26 | 2016/08/22 13:55 | Andrea Vavassori v Stefano Reitano | 6-3,6-3 |