Round: 25 Ground: Hardcourt outdoor
| Challenger Caltanissetta | 2016/06/07 18:35 | Marko Tepavac v Antonio Massara | 6-4,6-4 |
| Challenger Caltanissetta Qual | 2016/06/05 10:00 | Sergio Galdos v Antonio Massara | 3-6,3-6 |
| Challenger Caltanissetta Qual | 2016/06/04 13:05 | Antonio Massara v Riccardo Ghedin | 6-7,6-4,6-0 |
| Challenger Caltanissetta Qual | 2016/06/04 08:00 | Antonio Massara v Eduardo Dischinger | 6-4,6-2 |
| ITF Italy F13 | 2016/05/31 09:35 | Maverick Banes v Antonio Massara | 7-5,6-4 |
| ITF Italy F10 | 2016/05/10 07:30 | Mateo Nicolas Martinez v Antonio Massara | 6-3,6-2 |
| ITF Italy F9 | 2016/05/04 07:30 | Gian Marco Moroni v Antonio Massara | 7-5,6-2 |
| ITF Italy F9 | 2016/05/03 08:00 | Sergio Martos Gornes v Antonio Massara | 0-6,2-6 |
| ITF Turkey F22 | 2016/06/02 11:30 | Mitchell Thomas McDaniels v Francesco Vilardo | 3-6,7-5,2-6 |
| ITF Turkey F22 | 2016/06/01 13:40 | Mitchell Thomas McDaniels v Stephen Kaldawi | 6-1,7-6 |
| ITF Turkey F22 | 2016/05/30 11:30 | Mitchell Thomas McDaniels v Scott Duncan | 6-1,6-4 |
| ITF Turkey F21 | 2016/05/25 09:15 | Mitchell Thomas McDaniels v Christopher Heyman | 4-6,4-6 |
| ITF Turkey F20 | 2016/05/17 09:50 | Dimitar Kuzmanov v Mitchell Thomas McDaniels | 6-2,6-1 |
| ITF Turkey F20 Qual | 2016/05/16 10:00 | Mitchell Thomas McDaniels v Y Rogusskiy | 6-3,7-6 |
| ITF Turkey F10 | 2016/03/09 11:35 | Mitchell Thomas McDaniels v Nerman Fatic | 2-6,1-6 |
| ITF Turkey F10 | 2016/03/07 09:00 | Mitchell Thomas McDaniels v Nicolas Grandjean | 2-6,6-1,6-3 |