Face à face
| ITF Serbia F1 | 2014/06/11 11:30 | Milan Drinic v Nikola Milojevic | 0-6,2-6 |
Home History
| Eastern European Championship | 2020/06/16 12:00 | Nikola Milojevic v Eric Vanshelboim | 6-2,6-0 |
| Eastern European Championship | 2020/06/15 12:00 | Miomir Kecmanovic v Nikola Milojevic | 6-1,7-6 |
| Adria Tour | 2020/06/13 17:00 | Grigor Dimitrov v Nikola Milojevic | 1-4,3-4 |
| Adriatic Tennis Series | 2020/06/12 10:00 | Damir Dzumhur v Nikola Milojevic | 0-6,6-3,6-2 |
| Adriatic Tennis Series | 2020/06/11 09:00 | Petrovic, Danilo v Nikola Milojevic | 5-7,3-6 |
| Adriatic Tennis Series | 2020/06/10 11:30 | Eric Vanshelboim v Nikola Milojevic | 0-6,4-6 |
| Adriatic Tennis Series | 2020/06/09 10:30 | Cacic, Nikola v Nikola Milojevic | 3-6,3-6 |
| Challenger - Bengaluru | 2020/02/12 06:40 | Benjamin Bonzi v Nikola Milojevic | 6-4,6-1 |
Away History
| Eastern European Championship | 2020/06/16 13:30 | Miomir Kecmanovic v Milan Drinic | 6-2,6-0 |
| Eastern European Championship | 2020/06/15 12:00 | Eric Vanshelboim v Milan Drinic | 6-1,6-1 |
| Adriatic Tennis Series | 2020/06/08 09:20 | Milan Drinic v Zekic, Miljan | 2-6,0-6 |
| ITF M15 Novi Sad | 2019/08/15 08:00 | Huertas Del Pino Cordova, Arklon v Milan Drinic | 6-3,6-2 |
| ITF M15 Novi Sad | 2019/08/14 08:15 | Dica , Nini Gabriel v Milan Drinic | 6-1,1-6,2-6 |
| ITF M15 Novi Sad | 2019/08/07 09:55 | Zekic, Miljan v Milan Drinic | 6-4,6-2 |
| ITF M15 Novi Sad | 2019/08/06 08:00 | Milan Drinic v Durguti, Besir | 6-2,0-6,10-6 |
| ITF M15 Novi Sad | 2019/08/05 08:00 | Milan Drinic v Samuel Puskar | 6-3,6-1 |