Round: 46 Ground: Clay
| 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 Dominican Republic F3 | 2015/12/15 14:00 | Liam Caruana v Juan Ignacio Galarza | 5-7,2-6 |
| ITF Italy F11 | 2016/05/20 15:00 | Gianluca Di Nicola v Yannick Maden | 0-6,6-4,6-2 |
| ITF Italy F11 | 2016/05/19 08:00 | Cristian Rodriguez v Yannick Maden | 6-4,3-6,4-6 |
| Challenger Heilbronn | 2016/05/12 11:35 | Yannik Reuter v Yannick Maden | 6-3,6-4 |
| Challenger Heilbronn | 2016/05/10 09:00 | Go Soeda v Yannick Maden | 4-6,5-7 |
| ITF Italy F8 | 2016/04/30 08:00 | Francisco Bahamonde v Yannick Maden | 6-3,3-6,0-6 |
| ITF Italy F8 | 2016/04/29 08:00 | Yannick Maden v Gianluca Mager | 7-6,2-6,6-2 |
| ITF Italy F8 | 2016/04/28 12:05 | Franco Agamenone v Yannick Maden | 2-6,2-6 |
| ITF Italy F8 | 2016/04/27 11:30 | Corentin Moutet v Yannick Maden | 4-6,2-6 |