| Challenger Sibiu | 09/18 07:00 | 25 | [150] Nikola Milojevic v Alex Molcan [396] | 7-5,1-6,3-6 | |
| Challenger de Banja Luka | 09/11 14:10 | 25 | Nikola Milojevic v Marko Miladinovic | 2-6,2-6 | |
| US Open | 08/21 18:45 | 45 | [109] Gregoire Barrere v Nikola Milojevic [147] | 4-6,6-3,6-4 | |
| US Open | 08/19 18:00 | 44 | [235] Max Purcell v Nikola Milojevic [147] | 3-6,7-6,3-6 | |
| Challenger Manerbio | 08/07 11:10 | 25 | Nikola Milojevic v Zsombor Piros | Cancelled | |
| Challenger de Liberec | 08/04 10:00 | 29 | [236] Rogerio Dutra Silva v Nikola Milojevic [180] | 3-6,6-3,4-6 | |
| Challenger de Liberec | 08/03 11:00 | 28 | Nikola Milojevic v Pavel Nejedly | 6-0,4-6,7-5 | |
| Challenger de Liberec | 08/02 14:25 | 27 | [180] Nikola Milojevic v Jiri Vesely [135] | 7-6,1-6,6-2 | |
| Challenger de Liberec | 08/01 14:00 | 26 | [165] Federico Coria v Nikola Milojevic [180] | 6-7,3-6 | |
| Challenger de Liberec | 07/31 09:50 | 25 | [307] Carlos Taberner v Nikola Milojevic [180] | 7-5,3-6,6-7 | |
| Challenger de Praga | 07/25 13:25 | 26 | [188] Nikola Milojevic v Carlos Taberner [335] | 4-6,3-6 | |
| Challenger de Praga | 07/24 15:35 | 25 | [188] Nikola Milojevic v Jan Choinski [279] | 6-3,6-0 | |
| Wimbledon | 06/24 10:00 | 44 | [181] Nikola Milojevic v Mikael Torpegaard [172] | 6-4,6-7,3-6 | |
| Challenger Almaty | 06/07 05:00 | 27 | [153] Nikola Milojevic v Mario Vilella Martinez [292] | 4-6,3-6 | |
| Challenger Almaty | 06/06 08:05 | 26 | [153] Nikola Milojevic v Daniel Gimeno-Traver [258] | 6-1,3-6,6-3 | |
| Challenger Almaty | 06/04 06:00 | 25 | [153] Nikola Milojevic v Evan King [319] | 6-2,7-5 | |
| Open de Francia | 05/22 16:40 | 45 | [237] Mathias Bourgue v Nikola Milojevic [152] | 2-6,6-4,7-5 | |
| Open de Francia | 05/21 08:00 | 44 | [155] Egor Gerasimov v Nikola Milojevic [152] | 5-7,3-6 | |
| Challenger de Busan | 05/07 04:05 | 25 | [139] Nikola Milojevic v Yunseong Chung [270] | 2-6,6-3,5-7 | |
| Challenger de Seúl | 05/04 04:50 | 28 | [148] Nikola Milojevic v Max Purcell [268] | 2-6,0-6 | |
| Challenger de Seúl | 05/03 02:00 | 27 | [248] Zhe Li v Nikola Milojevic [148] | 4-6,5-7 | |
| Challenger de Seúl | 05/02 04:55 | 26 | [148] Nikola Milojevic v Sergiy Stakhovsky [115] | 6-2,7-6 | |
| Challenger de Seúl | 04/30 07:00 | 25 | Nikola Milojevic v Jea Moon Lee | 6-7,6-3,6-3 | |
| Challenger de Nanchang | 04/27 05:10 | 28 | [255] Andrej Martin v Nikola Milojevic [156] | 6-0,6-4 | |
| Challenger de Nanchang | 04/26 03:00 | 27 | [156] Nikola Milojevic v Andrew Harris [291] | 6-2,4-6,6-0 | |
| Challenger de Nanchang | 04/25 03:00 | 26 | [156] Nikola Milojevic v Akira Santillan [296] | 7-6,7-6 | |
| Challenger de Nanchang | 04/23 09:15 | 25 | [156] Nikola Milojevic v Sasi Kumar Mukund [270] | 6-2,6-4 | |
| Challenger de Anning | 04/19 05:30 | 27 | [164] Nikola Milojevic v Prajnesh Gunneswaran [80] | 5-7,3-6 | |
| Challenger de Anning | 04/18 03:00 | 26 | [245] Andrej Martin v Nikola Milojevic [164] | 1-6,7-6,1-6 | |
| Challenger de Anning | 04/17 03:05 | 25 | [252] Zhe Li v Nikola Milojevic [164] | 4-6,3-6 |