Round: 25 Ground: Hardcourt outdoor
| Challenger Rome 2 | 2016/09/27 12:30 | Jan Satral v Lorenzo Giustino | 6-0,6-4 |
| Challenger Sibiu | 2016/09/25 12:00 | Robin Haase v Lorenzo Giustino | 7-6,6-2 |
| Challenger Sibiu | 2016/09/24 11:20 | Lorenzo Giustino v Christopher O'Connell | 6-7,6-4,7-5 |
| Challenger Sibiu | 2016/09/23 12:10 | Jan Satral v Lorenzo Giustino | 4-6,6-3,3-6 |
| Challenger Sibiu | 2016/09/21 09:35 | Dragos Dima v Lorenzo Giustino | 6-4,6-7,1-6 |
| ITF Serbia F7 | 2016/09/18 10:00 | Lorenzo Giustino v Kristijan Mesaros | 3-6,6-2,6-4 |
| ITF Serbia F7 | 2016/09/17 12:00 | Lorenzo Giustino v Alexandar Lazarov | 6-4,6-4 |
| ITF Serbia F7 | 2016/09/16 09:00 | Lorenzo Giustino v Davide Galoppini | 6-1,6-2 |
| ITF Portugal F11 | 2016/09/28 13:35 | Yannick Mertens v Joao Monteiro | 6-3,6-4 |
| ITF Spain F29 | 2016/09/08 10:55 | Alberto Romero De Avila Senise v Joao Monteiro | 6-1,6-4 |
| ITF Spain F29 | 2016/09/07 12:05 | Joao Monteiro v Jaume Pla Malfeito | 6-3,3-6,6-3 |
| ITF Spain F29 | 2016/09/05 12:15 | Jonathan Morr v Joao Monteiro | 4-6,1-6 |
| ITF Spain F27 | 2016/08/23 16:30 | Joao Monteiro v Nicola Kuhn | 2-6,6-2,3-6 |
| ITF Spain F26 | 2016/08/19 15:40 | Joao Monteiro v Alberto Brizzi | 3-6,1-6 |
| ITF Spain F26 | 2016/08/18 15:10 | Javier Marti v Joao Monteiro | 6-4,2-6,1-6 |
| ITF Spain F26 | 2016/08/17 13:00 | Joao Monteiro v Eduard Esteve Lobato | 3-6,6-3,7-6 |