Round: 44 Ground: Clay
| ITF Macedonia F1 | 2016/07/03 08:00 | Domagoj Biljesko v Christos Keisidis | 7-6,6-4 |
| ITF Macedonia F2 | 2016/06/29 08:00 | Domagoj Biljesko v Libor Salaba | 4-6,4-6 |
| ITF Macedonia F2 | 2016/06/27 10:35 | Petar Conkic v Domagoj Biljesko | 2-6,5-7 |
| ITF Macedonia F2 | 2016/06/26 10:00 | David Micevski v Domagoj Biljesko | 2-6,1-6 |
| ITF Bosnia and Herzegovina F3 | 2016/05/24 12:55 | Sebastian Ofner v Domagoj Biljesko | 2-6,6-3,6-2 |
| ITF Bosnia and Herzegovina F3 Qual | 2016/05/23 09:00 | Domagoj Biljesko v Alen Rogic-Hadzalic | 4-6,6-0,6-1 |
| ITF Bosnia and Herzegovina F3 Qual | 2016/05/22 11:00 | Domagoj Biljesko v Lukasz Kozielski | 6-1,7-5 |
| ITF Bosnia and Herzegovina F2 | 2016/05/19 10:50 | Kristijan Mesaros v Domagoj Biljesko | 6-2,6-1 |
| ITF Macedonia F2 | 2016/06/26 12:00 | Christian Hirschmueller v Strahinja Rakic | 6-4,6-1 |
| ITF Macedonia F1 | 2016/06/21 14:00 | Strahinja Rakic v Giorgio Ricca | 6-4,3-6,2-6 |
| ITF Macedonia F1 Qual | 2016/06/20 08:00 | Strahinja Rakic v Keisuke Numajiri | 6-3,6-2 |
| ITF Macedonia F1 Qual | 2016/06/19 14:00 | Francesco Garzelli v Strahinja Rakic | 4-6,6-7 |
| ITF Serbia F8 | 2015/08/18 10:55 | Luka Ilic v Strahinja Rakic | 6-3,3-6,6-3 |
| ITF Serbia F8 | 2015/08/12 11:50 | Strahinja Rakic v Andre Biro | 0-6,6-3,3-6 |
| ITF Serbia F8 Qual | 2015/08/10 08:00 | Goran Markovic v Strahinja Rakic | 1-6,2-6 |
| ITF Serbia F8 Qual | 2015/08/09 08:00 | Strahinja Rakic v Ivan Goluza | 7-5,6-1 |