Round: 25 Ground: Clay
| ITF Italy F12 | 2016/05/28 13:00 | Marco Bortolotti v Stefanos Tsitsipas | 6-7,6-7 |
| ITF Italy F12 | 2016/05/27 15:30 | Lorenzo Frigerio v Marco Bortolotti | 5-7,1-6 |
| ITF Italy F12 | 2016/05/26 13:00 | Marco Bortolotti v Khumoyun Sultanov | 6-2,6-0 |
| ITF Italy F12 | 2016/05/25 12:50 | Marco Bortolotti v Filippo Baldi | 3-6,7-5,7-5 |
| ITF Italy F12 | 2016/05/24 09:40 | Marco Bortolotti v Orlando Luz | 6-3,3-6,6-2 |
| Challenger Mestre Qual | 2016/05/15 13:30 | Marco Bortolotti v Nicolas Jarry | 6-7,5-7 |
| Challenger Mestre Qual | 2016/05/14 14:25 | Marco Bortolotti v Walter Trusendi | 6-3,6-3 |
| Challenger Heilbronn Qual | 2016/05/07 15:15 | Peter Torebko v Marco Bortolotti | 4-6,6-4,7-5 |
| ITF Mexico F4 | 2016/05/24 19:00 | Alejandro Mendoza v Wilfredo Gonzalez | 6-4,1-6,7-6 |
| ITF Mexico F4 | 2016/05/22 15:00 | Wilfredo Gonzalez v Alonso A Delgado | 6-0,6-1 |
| ITF Greece F6 | 2016/04/24 09:30 | David Hopkins v Wilfredo Gonzalez | 6-2,6-3 |
| ITF Greece F6 | 2016/04/23 13:00 | Mats Rosenkranz v Wilfredo Gonzalez | 3-6,2-6 |
| ITF Greece F5 | 2016/04/20 08:30 | Wilfredo Gonzalez v Daniel Cukierman | 4-6,3-6 |
| ITF Greece F5 | 2016/04/18 09:20 | Karol Drzewiecki v Wilfredo Gonzalez | 6-4,3-6,4-6 |
| ITF Greece F4 | 2016/04/09 10:00 | Wilfredo Gonzalez v Aaron Addison | 6-3,2-6,6-7 |
| ITF Greece F3 | 2016/04/06 07:00 | Fred Simonsson v Wilfredo Gonzalez | 6-2,6-2 |