Round: 27 Ground: Hardcourt outdoor
| Challenger Poznan | 2016/07/15 13:50 | Aleksandr Nedovyesov v Nikola Milojevic | 5-7,6-2,6-3 |
| Challenger Poznan | 2016/07/13 11:30 | David Perez Sanz v Nikola Milojevic | 4-6,6-7 |
| Challenger Poznan | 2016/07/12 16:25 | Joris De Loore v Nikola Milojevic | 4-6,1-6 |
| ITF Netherlands F4 | 2016/07/06 09:00 | Nikola Milojevic v Botic Van De Zandschulp | 4-6,5-7 |
| ITF Netherlands F4 | 2016/07/05 10:00 | Nikola Milojevic v Colin Van Beem | 6-2,6-0 |
| ITF Tunisia F21 | 2016/06/05 09:30 | Nikola Milojevic v Cristian Garin | 4-6,6-2,0-6 |
| ITF Tunisia F21 | 2016/06/04 09:00 | Nikola Milojevic v Walter Trusendi | 6-2,5-7,6-4 |
| ITF Tunisia F21 | 2016/06/03 10:55 | Nikola Milojevic v Riccardo Sinicropi | 6-2,6-0 |
| Challenger Recanati Qual | 2016/07/16 13:05 | Lorenzo Frigerio v Filip Veger | 1-6,2-6 |
| ITF Egypt F14 | 2016/07/08 16:00 | Aldin Setkic v Lorenzo Frigerio | 7-5,7-6 |
| ITF Egypt F14 | 2016/07/07 17:50 | Quentin Robert v Lorenzo Frigerio | 4-6,4-6 |
| ITF Egypt F14 | 2016/07/06 16:00 | Issam Haitham Taweel v Lorenzo Frigerio | 1-6,4-6 |
| ITF Egypt F13 | 2016/07/01 17:45 | Aldin Setkic v Lorenzo Frigerio | 4-6,6-3,6-1 |
| ITF Egypt F13 | 2016/06/30 17:45 | Oleg Khotkov v Lorenzo Frigerio | 0-6,3-6 |
| ITF Egypt F13 | 2016/06/29 17:45 | Aria Harajchi v Lorenzo Frigerio | 2-6,1-6 |
| Challenger Milan Qual | 2016/06/18 12:35 | Juan Ignacio Galarza v Lorenzo Frigerio | 6-4,6-2 |