Round: 25 Ground: Clay
| Serbia F5, Singles | 2016/08/17 08:00 | Milenkovic, Nebojsa v Delic, Mate | 3-6,0-6 |
| ITF Serbia F1 Qual | 2016/07/16 07:30 | Rogic Hadzalic, Alen v Milenkovic, Nebojsa | 6-4,6-4 |
| ITF Serbia F6 | 2015/07/04 07:00 | Ivanov, Klim v Milenkovic, Nebojsa | 0-6,2-6 |
| ITF Serbia F2 Qual | 2015/06/13 13:00 | Bajic, Bogdan v Milenkovic, Nebojsa | 6-7,6-1,7-6 |
| ITF Serbia F8 | 2014/08/17 13:00 | Micevski, David v Milenkovic, Nebojsa | 6-3,6-0 |
| ITF Serbia F1 Qual | 2014/06/08 10:00 | Kijametovic, Aziz v Milenkovic, Nebojsa | 6-0,6-0 |
| ITF Austria F6 | 2016/08/13 09:30 | Koncilia, Lukas v Kaplja, Aljaz Jakob | 6-1,7-6 |
| ITF Austria F4 Qual | 2016/07/23 07:00 | Khrustalev, Nazar v Kaplja, Aljaz Jakob | 4-6,5-7 |
| ITF Germany F8 Qual | 2016/07/17 08:30 | Karlo Cubelic v Kaplja, Aljaz Jakob | 6-3,7-5 |
| ITF Bosnia and Herzegovina F2 Qual | 2016/05/15 08:00 | Kaplja, Aljaz Jakob v Orlita, Daniel | 7-6,1-6,2-6 |
| ITF Greece F5 | 2016/04/16 11:30 | Kaplja, Aljaz Jakob v Davies, George | 5-7,0-6 |
| ITF Croatia F3 | 2016/03/13 09:00 | Kaplja, Aljaz Jakob v Luigi Sorrentino | 1-6,2-6 |
| ITF Croatia F2 | 2016/03/06 11:30 | Baluda, Victor v Kaplja, Aljaz Jakob | 6-2,6-0 |
| ITF Croatia F2 | 2016/03/06 08:30 | Kaplja, Aljaz Jakob v Querol Cherigny, Daniel | 6-0,6-4 |