Round: 26 Ground: Clay
| ITF Italy F29 | 2016/09/14 09:00 | Stefano Travaglia v Gianluca Di Nicola | 6-4,6-2 |
| ITF Italy F29 | 2016/09/13 10:00 | Gianluca Di Nicola v Gian Marco Moroni | 2-6,6-4,6-3 |
| ITF Italy F28 | 2016/09/08 10:00 | Gianluca Di Nicola v Andrea Pellegrino | 4-6,7-6,4-6 |
| ITF Italy F28 | 2016/09/07 09:00 | Gianluca Di Nicola v Matteo Trevisan | 7-5,7-5 |
| ITF Italy F26 | 2016/08/25 11:00 | Gianluca Di Nicola v Yannick Jankovits | 1-6,6-7 |
| ITF Italy F26 | 2016/08/24 13:00 | Gianluca Di Nicola v Viktor Durasovic | 6-7,6-0,6-3 |
| ITF Italy F26 | 2016/08/23 19:00 | Zhizhen Zhang v Gianluca Di Nicola | 3-6,6-1,5-7 |
| ITF Italy F25 | 2016/08/15 11:45 | Gianluca Di Nicola v Jose Hernandez-Fernandez | 1-6,4-6 |
| ITF Italy F30 | 2016/09/19 07:00 | Cristian Carli v Filippo Leonardi | 6-7,6-3,1-6 |
| ITF Italy F28 | 2016/09/07 09:00 | Filippo Leonardi v Tomas Barrios Vera | 6-7,1-6 |
| ITF Serbia F4 | 2016/08/12 08:00 | Stefano Travaglia v Filippo Leonardi | 6-4,6-4 |
| ITF Serbia F4 | 2016/08/11 09:00 | Filippo Leonardi v Maxime Janvier | 6-3,6-4 |
| ITF Serbia F4 | 2016/08/10 12:15 | Boris Butulija v Filippo Leonardi | 2-6,1-6 |
| ITF Serbia F3 | 2016/08/02 10:00 | Nicholas Horton v Filippo Leonardi | 6-2,2-6,6-3 |
| 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 |