Round: 25 Ground: Clay
| ITF Serbia F5 | 2016/08/17 08:00 | Nebojsa Milenkovic v Mate Delic | 3-6,0-6 |
| ITF Serbia F1 Qual | 2016/07/16 07:30 | Alen Rogic-Hadzalic v Nebojsa Milenkovic | 6-4,6-4 |
| ITF Serbia F6 | 2015/07/04 07:00 | Klim Ivanov v Nebojsa Milenkovic | 0-6,2-6 |
| ITF Serbia F2 Qual | 2015/06/13 13:00 | Bogdan Bajic v Nebojsa Milenkovic | 6-7,6-1,7-6 |
| ITF Serbia F8 | 2014/08/17 13:00 | David Micevski v Nebojsa Milenkovic | 6-3,6-0 |
| ITF Serbia F1 | 2014/07/13 10:30 | James Allemby v Nebojsa Milenkovic | 7-5,6-2 |
| ITF Serbia F1 Qual | 2014/06/08 10:00 | Aziz Kijametovic v Nebojsa Milenkovic | 6-0,6-0 |
| ITF Serbia F5 | 2016/08/18 10:05 | Stefano Travaglia v Christian Hirschmueller | 7-6,6-4 |
| ITF Serbia F5 | 2016/08/17 08:00 | Christian Hirschmueller v Darko Jandric | 2-6,6-3,6-4 |
| ITF Serbia F4 | 2016/08/10 07:30 | Nikola Cacic v Christian Hirschmueller | 2-6,7-5,6-3 |
| ITF Serbia F3 | 2016/08/03 11:20 | Christian Hirschmueller v Christopher O'Connell | 2-6,3-6 |
| ITF Macedonia F2 | 2016/06/28 08:45 | Christian Hirschmueller v Richard Gabb | 1-6,4-6 |
| ITF Macedonia F2 | 2016/06/27 08:45 | Christian Hirschmueller v Goran Markovic | 6-1,6-2 |
| ITF Macedonia F2 | 2016/06/26 12:00 | Christian Hirschmueller v Strahinja Rakic | 6-4,6-1 |
| ITF Macedonia F1 Qual | 2016/06/20 08:00 | Christian Hirschmueller v Giorgio Ricca | 3-6,3-6 |