Round: 25 Ground: Hardcourt outdoor
| ITF Egypt F16 | 2016/07/18 17:15 | Dzhavakian, Yurii v Di Prima, Marco | 4-6,6-3,1-6 |
| ITF Egypt F16 | 2016/07/17 17:00 | Di Prima, Marco v Gee, Dylan | 6-4,6-4 |
| Egypt F15, Singles Qualifying | 2016/07/11 16:00 | Danes, Alexandru v Di Prima, Marco | 6-2,4-6,7-5 |
| Challenger Caltanissetta Qual | 2016/06/04 10:55 | Bega, Alessandro v Di Prima, Marco | 6-1,6-4 |
| ITF Egypt F2 | 2016/01/24 08:00 | Mercuri, Fabio v Di Prima, Marco | 6-2,6-7,6-1 |
| ITF Egypt F1 | 2016/01/20 08:00 | Barbosa, Romain v Di Prima, Marco | 6-2,6-1 |
| ITF Spain F6 Qual | 2015/03/22 09:00 | Di Prima, Marco v Plaza, Santiago | 2-6,3-6 |
| ITF Egypt F30 | 2015/01/18 08:00 | Garzelli, Francesco v Di Prima, Marco | 6-1,6-1 |
| Egypt F15, Singles Qualifying | 2016/07/09 19:30 | Kovalevych, Dmytro v Oswald, Jack | 6-1,6-0 |
| Egypt F14, Singles Qualifying | 2016/07/03 18:00 | Oswald, Jack v Manish Sureshkumar | 1-6,2-6 |
| ITF USA F5 | 2016/01/22 19:00 | Callahan, Hunter v Oswald, Jack | 6-1,6-1 |
| ITF USA F4 | 2016/01/15 13:30 | Oswald, Jack v Richter, Rudy | 4-6,1-6 |
| ITF Indonesia F5 | 2015/12/12 09:30 | Didenko, Bogdan v Oswald, Jack | 6-2,6-4 |
| ITF Tunisia F33 | 2015/11/22 12:00 | Oswald, Jack v Prokopchuk, Alexey | 1-6,2-6 |
| ITF Tunisia F31 | 2015/11/07 09:00 | Oswald, Jack v Allemby, James | 4-6,0-6 |
| ITF Zimbabwe F1 Qual | 2015/06/14 09:00 | Moyano, Agustin v Oswald, Jack | 6-3,4-6,6-3 |