Round: 62 Ground: Clay
| ITF Serbia F6 | 2016/09/04 10:00 | Milos Nikolic v Anze Loviscek | 6-3,6-1 |
| ITF Serbia F5 | 2016/08/17 08:00 | Milos Nikolic v Thomas Statzberger | 3-6,2-6 |
| ITF Serbia F5 Qual | 2016/08/15 10:10 | Milos Nikolic v Rrezart Cungu | 1-6,2-6 |
| ITF Serbia F5 Qual | 2016/08/14 10:00 | Milos Nikolic v Ruslan Khunarikov | 6-0,6-0 |
| ITF Serbia F3 Qual | 2016/07/30 09:30 | Goran Markovic v Milos Nikolic | 7-5,6-4 |
| ITF Serbia F1 Qual | 2016/07/19 08:00 | Timo Stodder v Milos Nikolic | 6-2,6-2 |
| ITF Serbia F1 Qual | 2016/07/18 08:00 | Goran Radanovic v Milos Nikolic | 2-6,6-2,3-6 |
| ITF Macedonia F1 | 2016/07/03 08:00 | Ivan Saveljic v Milos Nikolic | 2-6,6-7 |
| ITF Serbia F6 | 2016/09/04 10:00 | Ruslan Khunarikov v Ivan Randjelovic | 4-6,6-4,3-6 |
| ITF Serbia F4 Qual | 2016/08/07 10:30 | Ivan Randjelovic v Goran Radanovic | 2-6,0-6 |
| ITF Serbia F2 Qual | 2016/07/24 10:30 | Ivan Randjelovic v Darko Bojanovic | 0-6,1-6 |
| ITF Serbia F1 Qual | 2016/07/16 07:30 | Ivan Randjelovic v Milos Dabic | 1-6,2-6 |
| ITF Bosnia and Herzegovina F3 Qual | 2016/05/21 08:00 | Samuel Hodor v Ivan Randjelovic | 6-3,6-2 |
| ITF Bosnia and Herzegovina F2 Qual | 2016/05/14 10:00 | Lukasz Kozielski v Ivan Randjelovic | 6-3,6-0 |
| ITF Italy F32 | 2016/04/30 08:00 | Ivan Randjelovic v Antun Vidak | 4-6,2-6 |
| ITF Serbia F8 | 2015/08/15 14:30 | Patrik Nema v Ivan Randjelovic | 6-2,6-2 |