1. Round | 21/07/2019 | Radnički Niš | - | Proleter Novi Sad | 3:0 | ||||
2. Round | 27/07/2019 | Crvena Zvezda | - | Radnički Niš | 2:0 | ||||
3. Round | 03/08/2019 | Radnički Niš | - | FK Javor | 2:1 | ||||
4. Round | 10/08/2019 | Radnički Niš | - | FK Voždovac | 2:1 | ||||
5. Round | 17/08/2019 | Mladost Lučani | - | Radnički Niš | 1:1 | ||||
6. Round | 25/08/2019 | Radnički Niš | - | Spartak Subotica | 2:1 | ||||
7. Round | 01/09/2019 | FK Čukarički | - | Radnički Niš | 1:0 | ||||
8. Round | 13/09/2019 | Radnički Niš | - | Vojvodina | 1:2 | ||||
9. Round | 21/09/2019 | FK Inđija | - | Radnički Niš | 0:1 | ||||
10. Round | 28/09/2019 | Radnički Niš | - | Partizan | 1:4 | ||||
11. Round | 05/10/2019 | FK Mačva Šabac | - | Radnički Niš | 0:1 | ||||
17. Round | 23/11/2019 | Radnički Niš | - | Crvena Zvezda | 0:2 |