Ground: Hardcourt outdoor
| ITF Italy F23 | 2014/07/15 11:25 | Filippo Leonardi v Marco Bortolotti | 6-3,6-2 |
| ITF Italy F20 | 2014/06/26 13:55 | Filippo Leonardi v Arthur De Greef | 4-6,4-6 |
| ITF Italy F18 | 2014/06/10 10:40 | Edoardo Eremin v Filippo Leonardi | 6-1,7-5 |
| ITF Italy F17 | 2014/06/03 10:25 | Nicolas Kicker v Filippo Leonardi | 2-6,6-3,6-4 |
| ITF Italy F16 | 2014/05/29 18:45 | Benjamin Mitchell v Filippo Leonardi | 3-6,6-4,6-1 |
| ITF Italy F15 | 2014/05/20 16:50 | Roberto Marcora v Filippo Leonardi | 6-4,7-6 |
| ITF Italy F13 | 2014/05/07 08:00 | Filippo Leonardi v Juan Lizariturry | 4-6,3-6 |
| ITF Italy F13 | 2014/05/06 08:00 | Andrea Grazioso v Filippo Leonardi | 2-6,2-6 |
| ITF Italy F24 Qual | 2014/07/20 08:00 | Antonio Massara v Francesco Ferrari | 6-2,6-2 |
| Challenger Recanati | 2014/07/15 16:10 | Antonio Massara v Filip Veger | 4-6,1-6 |
| ITF Italy F22 Qual | 2014/07/06 09:00 | Antonio Massara v Gianluca Beghi | 6-7,3-6 |
| ITF Italy F22 Qual | 2014/07/05 08:00 | Antonio Massara v Lorenzo Sonego | 3-6,6-3,6-2 |
| Challenger Todi | 2014/07/01 10:00 | Antonio Massara v Enrique Lopez-Perez | 0-6,4-6 |
| ITF Italy F17 | 2014/06/03 10:50 | Joao Pedro Sorgi v Antonio Massara | 2-6,6-7 |