Round: 28 Ground: Hardcourt outdoor
| ITF Portugal F10 | 2016/07/29 16:45 | Joao Domingues v Hannestad, Benjamin | 2-6,6-7 |
| ITF Portugal F10 | 2016/07/28 08:30 | Hannestad, Benjamin v Zgombic, Fran Zvonimir | 6-3,6-2 |
| ITF Portugal F10 | 2016/07/26 17:30 | Poncelet, Victor v Hannestad, Benjamin | 6-2,0-6,2-6 |
| ITF Portugal F10 | 2016/07/25 10:30 | Hannestad, Benjamin v Syromolotov Netrebin, Yuri | 6-7,1-6 |
| ITF Portugal F9 | 2016/07/19 08:30 | Hannestad, Benjamin v Voljacques, Hugo | 1-6,6-7 |
| ITF Portugal F9 | 2016/07/18 12:30 | Hannestad, Benjamin v Oakley, Luke | 6-3,6-7,6-2 |
| ITF USA F15 Qual | 2016/04/25 15:00 | Torre, Eduardo Agustin v Hannestad, Benjamin | 2-6,6-3,6-2 |
| ITF USA F15 Qual | 2016/04/24 16:00 | Ely, Andrew v Hannestad, Benjamin | 1-6,0-6 |
| ITF Portugal F10 | 2016/07/29 08:30 | Nuno Borges v O'Mara, Jonny | 1-6,6-1,5-7 |
| ITF Portugal F10 | 2016/07/28 08:30 | Shcherba, Vitalii v O'Mara, Jonny | 1-6,0-6 |
| ITF Portugal F9 | 2016/07/21 08:30 | O'Mara, Jonny v Patael, Ben | 6-7,4-6 |
| ITF Portugal F9 | 2016/07/20 08:30 | O'Mara, Jonny v Poncelet, Victor | 6-4,7-5 |
| ITF Portugal F6 | 2016/05/20 10:00 | O'Mara, Jonny v Crepaldi, Erik | 4-6,6-4,3-6 |
| ITF Portugal F6 | 2016/05/18 16:30 | Cacao, Tiago v O'Mara, Jonny | 1-6,0-6 |
| ITF Portugal F5 | 2016/05/12 17:00 | Dubail, Julien v O'Mara, Jonny | 6-1,6-4 |
| ITF Portugal F5 | 2016/05/12 10:30 | O'Mara, Jonny v Clayton, Scott | 4-6,6-3,6-3 |