Round: 25 Ground: Clay
| Challenger Perugia Qual | 2016/06/11 11:05 | Liam Caruana v Yannick Maden | 2-6,4-6 |
| ITF Italy F12 | 2016/05/26 18:40 | Stefanos Tsitsipas v Liam Caruana | 6-4,6-4 |
| ITF Italy F12 | 2016/05/24 11:00 | Thales Turini v Liam Caruana | 3-6,4-6 |
| ITF USA F11 Qual | 2016/03/20 16:00 | Joao Pedro Sorgi v Liam Caruana | 6-4,6-4 |
| ITF USA F2 | 2016/01/13 18:00 | Liam Caruana v Gonzales Austin | 7-6,3-6,6-4 |
| ITF USA F2 Qual | 2016/01/09 18:00 | Yaseen Elhalafawy v Liam Caruana | 0-6,0-6 |
| ITF USA F1 Qual | 2016/01/04 17:00 | Yannick Hanfmann v Liam Caruana | 6-2,6-0 |
| ITF USA F1 Qual | 2016/01/02 17:00 | Bjorn Hoffmann v Liam Caruana | 6-7,3-6 |
| 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 |
| ITF Bosnia and Herzegovina F3 Qual | 2016/05/22 09:00 | Gianluca Acquaroli v Dusan Rajic | 3-6,3-6 |