| Open de Australia | 01/12 14:55 | 15 | [182] Frederico Ferreira Silva v Nikola Milojevic [138] | 2-6,6-1,6-4 | |
| Open de Australia | 01/11 12:10 | 60 | [220] Matteo Viola v Nikola Milojevic [138] | 4-6,4-6 | |
| Challenger de Maia | 11/30 13:45 | 25 | [138] Nikola Milojevic v Marco Trungelliti [253] | 3-6,1-6 | |
| Challenger de Bratislava | 11/12 09:00 | 26 | [232] Matteo Viola v Nikola Milojevic [136] | 7-6,4-6,6-3 | |
| Challenger de Bratislava | 11/10 14:55 | 25 | [272] Andrea Arnaboldi v Nikola Milojevic [136] | 5-7,6-7 | |
| Challenger de Parma 2 | 11/02 11:20 | 25 | [231] Constant Lestienne v Nikola Milojevic [137] | 7-6,7-5 | |
| Challenger de Hamburgo | 10/30 15:10 | 27 | [105] Kamil Majchrzak v Nikola Milojevic [137] | 6-3,6-1 | |
| Challenger de Hamburgo | 10/28 09:00 | 26 | [273] Pavel Kotov v Nikola Milojevic [137] | 6-7,1-6 | |
| Challenger de Hamburgo | 10/26 12:20 | 25 | [190] Lukas Lacko v Nikola Milojevic [137] | 5-7,4-6 | |
| ATP San Petersburgo | 10/11 10:00 | 164 | [144] Nikola Milojevic v Nino Serdarusic [307] | 7-6,2-6,2-6 | |
| ATP San Petersburgo | 10/10 08:00 | 64 | Nikola Milojevic v Evgeny Karlovskiy | 6-4,6-0 | |
| Open de Francia | 10/01 13:05 | 24 | [144] Nikola Milojevic v Aljaz Bedene [56] | 5-7,6-2,1-6,6-7 |