Round: 26 Ground: Clay
| ITF Italy F20 | 2017/07/05 11:10 | Giacalone, Omar v Leonardi, Filippo | 7-5,2-6,3-6 |
| ITF Italy F7 | 2015/05/01 09:30 | Giacalone, Omar v Leonardi, Filippo | 6-4,7-6 |
| ITF Italy F21 | 2017/07/11 13:15 | Dima, Dragos v Giacalone, Omar | 4-6,3-6 |
| ITF Italy F20 | 2017/07/05 11:10 | Giacalone, Omar v Leonardi, Filippo | 7-5,2-6,3-6 |
| ITF Italy F20 | 2017/07/04 08:00 | Giacalone, Omar v Marson, Guido | 6-3,6-2 |
| Challenger Milan Qual | 2017/06/24 08:30 | Pospisil, Jaroslav v Giacalone, Omar | 6-2,6-1 |
| Challenger Todi Qual | 2017/06/17 13:35 | Haider-Maurer, Andreas v Giacalone, Omar | 6-3,6-4 |
| Tunisia F22, Singles Qualifying | 2017/06/07 09:30 | Manuel Guinard v Giacalone, Omar | 7-5,6-7,6-1 |
| Challenger - Francavilla | 2017/04/25 11:30 | Ramirez Hidalgo, Ruben v Giacalone, Omar | 3-6,7-6,6-3 |
| Challenger Francavilla Qual | 2017/04/24 09:00 | Petr Michnev v Giacalone, Omar | 2-6,1-6 |
| ITF Italy F21 | 2017/07/11 11:30 | Prevosto, Luca v Leonardi, Filippo | 7-6,4-6,3-6 |
| ITF Italy F20 | 2017/07/08 15:00 | Andrea Collarini v Leonardi, Filippo | 6-3,6-3 |
| ITF Italy F20 | 2017/07/07 12:00 | Leonardi, Filippo v Santanna, B. | 7-5,7-6 |
| ITF Italy F20 | 2017/07/06 12:00 | Leonardi, Filippo v Andrea Guerrieri | 6-3,6-0 |
| ITF Italy F20 | 2017/07/05 11:10 | Giacalone, Omar v Leonardi, Filippo | 7-5,2-6,3-6 |
| ITF Italy F20 | 2017/07/04 12:30 | Marcora, Roberto v Leonardi, Filippo | 4-6,5-7 |
| ITF Italy F20 | 2017/07/02 10:00 | Leonardi, Filippo v Vidal, Nicola | 6-1,6-1 |
| ITF Italy F20 | 2017/07/01 11:30 | Leonardi, Filippo v Roggero, Tommaso | 6-2,6-2 |