Round: 25 Ground: Clay
| ITF Serbia F1 | 2016/07/22 08:00 | Christopher O'Connell v Tomislav Jotovski | 6-4,6-0 |
| ITF Serbia F1 | 2016/07/21 08:00 | Tomislav Jotovski v Manuel Pena Lopez | 6-2,6-3 |
| ITF Serbia F1 | 2016/07/20 10:30 | Tomislav Jotovski v Timur Kiyamov | 6-2,6-2 |
| ITF Macedonia F1 | 2016/07/07 10:45 | Richard Gabb v Tomislav Jotovski | 6-3,6-4 |
| ITF Macedonia F1 | 2016/07/05 08:30 | Stefan Micov v Tomislav Jotovski | 3-6,4-6 |
| ITF Macedonia F2 | 2016/07/01 13:00 | Kristijan Mesaros v Tomislav Jotovski | 6-0,6-0 |
| ITF Macedonia F2 | 2016/06/30 10:00 | Tomislav Jotovski v Libor Salaba | 6-3,3-6,6-1 |
| ITF Macedonia F2 | 2016/06/28 09:25 | Gabriel Donev v Tomislav Jotovski | 4-6,1-6 |
| ITF Italy F21 | 2016/07/18 15:00 | Omar Giacalone v Alessandro Luisi | 6-1,6-0 |
| ITF Italy F20 | 2016/07/11 12:30 | Davide Galoppini v Alessandro Luisi | 6-2,6-0 |
| ITF Poland F4 | 2016/06/14 11:10 | Patrik Niklas-Salminen v Alessandro Luisi | 6-4,6-3 |
| ITF Poland F3 | 2016/06/08 09:00 | Alessandro Luisi v David Poljak | 6-2,4-6,3-6 |
| ITF Poland F2 | 2016/05/31 08:00 | Michal Dembek v Alessandro Luisi | 6-3,6-3 |
| ITF Italy F11 | 2016/05/17 12:15 | Alessandro Luisi v Daniele Capecchi | 5-7,2-6 |
| ITF Tunisia F18 | 2016/05/11 10:10 | Alessandro Luisi v Pedro Sousa | 1-6,6-4,4-6 |
| ITF Tunisia F17 | 2016/05/06 09:00 | Karim Hossam v Alessandro Luisi | 6-4,6-1 |