Round: 29 Ground: Clay
| ITF Italy F22 | 2016/07/30 19:20 | Galoppini, Davide v Giacalone, Omar | 4-6,3-6 |
| ITF Italy F22 | 2016/07/29 16:00 | Giacalone, Omar v Sinicropi, Riccardo | 6-3,6-4 |
| ITF Italy F22 | 2016/07/26 17:45 | Giacalone, Omar v Cammarata, Alberto | 6-2,5-7,6-0 |
| ITF Italy F21 | 2016/07/21 12:30 | Giacalone, Omar v Jacq, Gregoire | 3-6,4-6 |
| ITF Italy F21 | 2016/07/20 12:30 | Giacalone, Omar v Carli, Christian | 6-2,6-4 |
| ITF Italy F21 | 2016/07/18 15:00 | Giacalone, Omar v Luisi, Alessandro | 6-1,6-0 |
| ITF Italy F20 | 2016/07/13 12:00 | Andrea Pellegrino v Giacalone, Omar | 6-2,6-3 |
| ITF Italy F20 | 2016/07/11 12:30 | Spinnato, Daniele v Giacalone, Omar | 2-6,2-6 |
| ITF Italy F22 | 2016/07/30 16:00 | Antonio Massara v Basso, Andrea | 6-7,6-3,4-6 |
| ITF Italy F22 | 2016/07/29 19:30 | Basso, Andrea v Bortolotti, Marco | 6-2,7-6 |
| ITF Italy F22 | 2016/07/27 11:20 | Roncalli, Simone v Basso, Andrea | 5-7,1-6 |
| ITF Italy F22 | 2016/07/25 09:30 | Fellin, Manfred v Basso, Andrea | 1-6,2-6 |
| ITF Italy F21 | 2016/07/21 13:30 | Federico Coria v Basso, Andrea | 3-6,6-4,7-5 |
| ITF Italy F21 | 2016/07/20 20:00 | Gabrieli, Tommaso v Basso, Andrea | 1-6,1-6 |
| ITF Italy F21 | 2016/07/19 13:35 | Basso, Andrea v Trusendi, Walter | 6-2,6-3 |
| Challenger San Benedetto | 2016/07/12 14:40 | Basso, Andrea v de Greef, Arthur | 6-4,4-6,4-6 |