Round: 25 Ground: Clay
| ITF Italy F19 | 2016/07/06 13:55 | Liam Caruana v Cristian Garin | 6-7,3-6 |
| ITF Italy F19 | 2016/07/04 09:00 | Liam Caruana v Gianluca Acquaroli | 6-3,6-0 |
| 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 Italy F20 | 2016/07/16 17:00 | Andrea Pellegrino v Francisco Bahamonde | 6-4,5-7,6-4 |
| ITF Italy F20 | 2016/07/15 15:30 | Francesco Picco v Francisco Bahamonde | 3-6,5-7 |
| ITF Italy F20 | 2016/07/14 12:30 | Franco Agamenone v Francisco Bahamonde | 6-4,3-6,1-6 |
| ITF Italy F20 | 2016/07/12 10:00 | Luca Prevosto v Francisco Bahamonde | 6-7,2-6 |
| Challenger Vicenza | 2016/05/24 10:20 | Alejandro Gonzalez v Francisco Bahamonde | 7-6,4-6,6-4 |
| ITF Italy F11 | 2016/05/21 12:00 | Francisco Bahamonde v Daniele Capecchi | 3-6,5-7 |
| ITF Italy F11 | 2016/05/20 09:30 | Francisco Bahamonde v Andrea Pellegrino | 7-5,7-5 |
| ITF Italy F11 | 2016/05/19 11:05 | Francisco Bahamonde v Cristian Carli | 6-1,6-4 |