Round: 27 Ground: Hardcourt outdoor
| 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 |
| ITF Portugal F5 Qual | 2016/05/10 10:00 | O'Mara, Jonny v Redondo Pereira, Sergio | 6-1,6-1 |
| ITF Portugal F5 Qual | 2016/05/09 09:00 | O'Mara, Jonny v von Hafe Perez, Jose | 6-1,6-2 |
| ITF Greece F5 | 2016/04/24 07:00 | O'Mara, Jonny v Glasspool, Lloyd | 3-6,6-4,6-7 |
| ITF Greece F5 | 2016/04/22 07:00 | Libietis, Mikelis v O'Mara, Jonny | 3-6,5-7 |
| ITF Greece F5 | 2016/04/21 07:00 | Fabian, Patrik v O'Mara, Jonny | 3-6,6-7 |
| ITF Portugal F6 | 2016/05/19 14:00 | Cunha-Silva, Felipe v Crepaldi, Erik | 2-6,3-6 |
| ITF Portugal F6 | 2016/05/17 12:00 | Hernando Ruano, Jorge v Crepaldi, Erik | 6-4,3-6,6-7 |
| Italie F10, Qualifications Simples | 2016/05/10 13:40 | Luca Tomasetto v Crepaldi, Erik | 6-3,6-3 |
| ITF Italy F9 | 2016/05/06 08:30 | Casper Ruud v Crepaldi, Erik | 4-6,6-7 |
| ITF Italy F7 | 2016/04/19 12:05 | Crepaldi, Erik v Enzo Couacaud | 2-6,1-6 |
| ITF Italy F6 | 2016/04/16 09:00 | Crepaldi, Erik v Stefanos Tsitsipas | 3-6,1-6 |
| ITF Italy F6 | 2016/04/15 08:00 | Leonardi, Filippo v Crepaldi, Erik | 2-6,2-6 |
| ITF Italy F6 | 2016/04/14 11:10 | Crepaldi, Erik v Turini, Thales | 6-0,6-3 |