Round: 47 Ground: Clay
| 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 Macedonia F2 | 2016/06/26 14:00 | Gabriel Donev v Milos Nikolic | 6-3,6-4 |
| ITF Macedonia F2 | 2016/06/25 14:00 | Luka Pavlovic v Milos Nikolic | 0-6,3-6 |
| ITF Macedonia F1 Qual | 2016/06/19 07:00 | Milos Nikolic v Goran Markovic | 3-6,2-6 |
| ITF Macedonia F1 Qual | 2016/06/18 08:00 | Milos Nikolic v Yuichiro Inui | 4-6,6-1,6-2 |
| ITF Serbia F5 Qual | 2016/08/13 09:30 | Philip Sikman v Ruslan Khunarikov | 6-1,4-6,2-6 |
| ITF Austria F5 Qual | 2016/08/06 08:30 | Ruslan Khunarikov v Sandro Kopp | 6-3,6-3 |
| ITF Croatia F4 Qual | 2015/03/09 09:00 | Ruslan Khunarikov v Mattia Bedolo | 6-4,3-6,5-7 |