Round: 54 Ground: Clay
| Challenger Recanati Qual | 2016/07/16 10:45 | Tommaso Compagnucci v Viktor Galovic | 1-6,2-6 |
| ITF Italy F22 Qual | 2016/07/23 12:10 | Luca Prevosto v Gianluca Acquaroli | 6-3,7-6 |
| ITF Italy F21 | 2016/07/18 14:45 | Gianluca Acquaroli v Alessandro Colella | 6-7,3-6 |
| ITF Italy F21 Qual | 2016/07/17 09:30 | Alberto Cammarata v Gianluca Acquaroli | 6-7,6-4,4-6 |
| ITF Italy F19 | 2016/07/04 09:00 | Liam Caruana v Gianluca Acquaroli | 6-3,6-0 |
| ITF Italy F19 | 2016/07/03 09:40 | Gianluca Acquaroli v Giovanni Oradini | 0-6,6-4,6-4 |
| ITF Czech Republic F4 Qual | 2016/06/25 11:00 | Matej Vocel v Gianluca Acquaroli | 6-2,6-1 |
| ITF Czech Republic F4 Qual | 2016/06/25 08:00 | Karol Krawczynski v Gianluca Acquaroli | 6-4,4-6,2-6 |
| ITF Romania F5 | 2016/06/04 10:30 | Gianluca Acquaroli v Sorin Andrei Iordache | 6-3,2-6,5-7 |