Round: 25 Ground: Hardcourt outdoor
| ITF Portugal F7 Qual | 2016/05/22 14:00 | Daniel Hobart v David Redondo Pereira | 6-1,6-3 |
| ITF Portugal F7 Qual | 2016/05/21 12:30 | Daniel Hobart v Abdulhameed Alshatti | 6-1,6-1 |
| ITF Portugal F6 Qual | 2016/05/16 13:00 | Felipe Cunha Silva v Daniel Hobart | 7-5,6-3 |
| ITF Portugal F6 Qual | 2016/05/15 10:00 | Pedro Estevao v Daniel Hobart | 2-6,3-6 |
| ITF Portugal F6 Qual | 2016/05/14 11:30 | Pedro Gabriel Rodrigues v Daniel Hobart | 6-4,2-6,2-6 |
| ITF Portugal F5 Qual | 2016/05/10 13:00 | Nuno Deus v Daniel Hobart | 6-2,6-3 |
| ITF Portugal F4 | 2016/05/03 13:00 | Duarte Vale v Daniel Hobart | 6-2,6-0 |
| ITF Greece F6 | 2016/04/25 11:40 | Yusuke Takahashi v Daniel Hobart | 4-6,7-6,6-3 |
| ITF Portugal F6 | 2016/05/19 11:00 | Joao Domingues v Bruno Santanna | 7-6,2-6,6-4 |
| ITF Portugal F6 | 2016/05/17 12:00 | Goncalo Falcao v Bruno Santanna | 2-6,4-6 |
| ITF Portugal F4 | 2016/05/09 22:00 | Joao Domingues v Bruno Santanna | 6-7,2-6 |
| ITF Portugal F4 | 2016/05/09 17:20 | Bruno Santanna v Ricardo Ojeda Lara | 4-6,6-3,10-5 |
| ITF Portugal F4 | 2016/05/08 18:25 | Duarte Vale v Bruno Santanna | 6-7,6-2,3-10 |
| ITF Portugal F4 | 2016/05/04 11:00 | Bruno Santanna v Thales Turini | 6-2,6-2 |
| ITF Greece F6 | 2016/04/28 07:00 | Stefanos Tsitsipas v Bruno Santanna | 6-3,7-6 |
| ITF Greece F6 | 2016/04/26 10:20 | Filippo Baldi v Bruno Santanna | 6-7,6-2,1-6 |