Round: 25 Ground: Clay
| ITF Italy F21 | 2016/07/18 19:30 | Benjamin Bonzi v Filippo Leonardi | 6-4,6-1 |
| ITF Austria F2 | 2016/07/11 10:30 | Filippo Leonardi v Nik Razborsek | 0-6,4-6 |
| ITF Italy F12 | 2016/05/24 12:10 | Filippo Leonardi v Claudio Fortuna | 4-6,3-6 |
| ITF Italy F11 | 2016/05/19 09:55 | Daniele Capecchi v Filippo Leonardi | 6-4,6-1 |
| ITF Italy F10 | 2016/05/10 10:20 | Filippo Leonardi v Nicola Ghedin | 3-6,2-6 |
| ITF Italy F7 | 2016/04/20 10:45 | Riccardo Bonadio v Filippo Leonardi | 6-4,6-4 |
| ITF Italy F7 | 2016/04/18 09:45 | Demian Raab v Filippo Leonardi | 2-6,1-6 |
| ITF Italy F6 | 2016/04/15 08:00 | Filippo Leonardi v Erik Crepaldi | 2-6,2-6 |
| ITF Italy F22 Qual | 2016/07/24 08:00 | Marco De Rossi v Francesco Moncagatto | 1-6,4-6 |
| ITF Italy F22 Qual | 2016/07/23 07:00 | Marco Miceli v Francesco Moncagatto | 3-6,2-6 |
| ITF Italy F21 | 2016/07/18 17:00 | Alexandre Muller v Francesco Moncagatto | 6-4,6-0 |
| ITF Italy F21 Qual | 2016/07/17 09:30 | Giovanni Rizzuti v Francesco Moncagatto | 6-2,6-4 |
| ITF Italy F21 Qual | 2016/07/16 08:00 | Andrea Caligiana v Francesco Moncagatto | 4-6,4-6 |
| ITF Italy F20 Qual | 2016/07/10 10:00 | Francesco Moncagatto v Samuele Ramazzotti | 2-6,1-6 |
| ITF Italy F16 Qual | 2016/06/18 08:00 | Alessandro Ceppellini v Francesco Moncagatto | 4-6,6-4,6-3 |
| ITF Italy F15 | 2016/06/11 07:30 | Francesco Moncagatto v Blake Ellis | 4-6,6-7 |