Round: 25 Ground: Clay
| ITF Italy F32 | 2016/05/20 08:30 | Christopher O'Connell v Tobias Simon | 7-5,7-6 |
| ITF Italy F32 | 2016/05/19 10:50 | Jonathan Mridha v Tobias Simon | 4-6,2-6 |
| ITF Italy F32 | 2016/05/17 11:05 | Tobias Simon v Tomislav Ternar | 4-6,6-1,6-1 |
| ITF Italy F32 | 2016/05/13 08:00 | Tobias Simon v Nikola Cacic | 6-4,3-6,3-6 |
| ITF Italy F32 | 2016/05/12 08:00 | Tobias Simon v Florian Fallert | 2-6,6-1,7-5 |
| ITF Italy F32 | 2016/05/11 10:00 | Tallon Griekspoor v Tobias Simon | 6-3,4-6,5-7 |
| ITF Italy F32 | 2016/05/05 11:10 | Christopher O'Connell v Tobias Simon | 6-4,3-6,6-1 |
| ITF Qatar F2 | 2016/04/12 22:00 | James Marsalek v Tobias Simon | 6-4,7-6 |
| ITF Italy F13 | 2016/05/30 12:00 | Fernando Romboli v Thales Turini | 2-6,4-6 |
| ITF Italy F11 | 2016/05/18 10:00 | Fernando Romboli v Luca Pancaldi | 2-6,3-6 |
| ITF Spain F13 | 2016/05/10 09:00 | Carlos Taberner v Fernando Romboli | 6-4,6-1 |
| Challenger Rome Qual | 2016/04/30 12:45 | Evgeny Karlovskiy v Fernando Romboli | 6-2,7-5 |
| ITF France F9 | 2016/04/26 11:40 | Fernando Romboli v Zhizhen Zhang | 7-5,3-6,2-6 |
| ITF France F8 | 2016/04/20 13:40 | Fernando Romboli v Alexandre Penaud | 2-6,6-7 |
| ITF France F8 | 2016/04/19 13:30 | Fernando Romboli v Fabien Reboul | 6-3,6-7,6-4 |
| ITF Italy F6 | 2016/04/12 07:30 | Michal Schmid v Fernando Romboli | 6-1,6-0 |