| Open d'Australie, Melbourne, Australie | 01/12 14:55 | 15 | [182] Ferreira Silva, Frederico v Milojevic, Nikola [138] | 2-6,6-1,6-4 | |
| Open d'Australie, Melbourne, Australie | 01/11 12:10 | 60 | [220] Viola, Matteo v Milojevic, Nikola [138] | 4-6,4-6 | |
| Maia, Portugal | 11/30 13:45 | 25 | [138] Milojevic, Nikola v Trungelliti, Marco [253] | 3-6,1-6 | |
| Bratislava, Slovaquie | 11/12 09:00 | 26 | [232] Viola, Matteo v Milojevic, Nikola [136] | 7-6,4-6,6-3 | |
| Bratislava, Slovaquie | 11/10 14:55 | 25 | [272] Arnaboldi, Andrea v Milojevic, Nikola [136] | 5-7,6-7 | |
| Challenger Parma 2 | 11/02 11:20 | 25 | [231] Lestienne, Constant v Milojevic, Nikola [137] | 7-6,7-5 | |
| Hambourg, Allemagne | 10/30 15:10 | 27 | [105] Majchrzak, Kamil v Milojevic, Nikola [137] | 6-3,6-1 | |
| Hambourg, Allemagne | 10/28 09:00 | 26 | [273] Kotov, Pavel v Milojevic, Nikola [137] | 6-7,1-6 | |
| Hambourg, Allemagne | 10/26 12:20 | 25 | [190] Lacko, Lukas v Milojevic, Nikola [137] | 5-7,4-6 | |
| Saint-Pétersbourg, Russie | 10/11 10:00 | 164 | [144] Milojevic, Nikola v Serdarusic, Nino [307] | 7-6,2-6,2-6 | |
| Saint-Pétersbourg, Russie | 10/10 08:00 | 64 | Milojevic, Nikola v Karlovskiy, Evgeny | 6-4,6-0 | |
| Roland-Garros, Paris, France | 10/01 13:05 | 24 | [144] Milojevic, Nikola v Bedene, Aljaz [56] | 5-7,6-2,1-6,6-7 |