Round: 44 Ground: Clay
| ITF Portugal F6 | 2016/05/18 11:10 | Guilherme W Osorio v Tak Khunn Wang | 3-6,3-6 |
| ITF Portugal F6 Qual | 2016/05/15 09:00 | Guilherme W Osorio v Marcus Walters | 6-3,6-4 |
| ITF Portugal F4 | 2016/05/09 10:00 | Guilherme W Osorio v Ricardo Ojeda Lara | 1-6,1-6 |
| ITF Portugal F4 | 2016/05/03 11:00 | Aaron Addison v Guilherme W Osorio | 3-6,5-7 |
| ITF Portugal F12 | 2015/09/30 11:00 | Jorge Hernando-Ruano v Guilherme W Osorio | 6-1,6-2 |
| ITF Portugal F12 Qual | 2015/09/28 09:00 | Guilherme W Osorio v Joao Antonio | 7-6,7-6 |
| ITF Portugal F6 | 2015/05/19 14:50 | Joao Antonio v Guilherme W Osorio | 2-6,1-6 |
| ITF Portugal F6 Qual | 2015/05/18 16:00 | Bruno Mardones v Guilherme W Osorio | 6-7,3-6 |
| ITF Macedonia F1 | 2016/07/07 08:30 | Luka Pavlovic v Neil Pauffley | 1-6,2-6 |
| ITF Macedonia F1 | 2016/07/06 13:45 | Luka Pavlovic v Dejan Katic | 7-6,6-4 |
| ITF Macedonia F1 | 2016/07/04 12:10 | Luka Pavlovic v Calin Manda | 7-6,6-3 |
| ITF Macedonia F1 | 2016/07/03 08:00 | Peter Bothwell v Luka Pavlovic | 4-6,2-6 |
| ITF Macedonia F1 | 2016/07/02 12:00 | Radoslav Shandarov v Luka Pavlovic | 2-6,1-6 |
| ITF Macedonia F2 | 2016/06/25 14:00 | Luka Pavlovic v Milos Nikolic | 0-6,3-6 |