| 1. Round | 21/07/2019 | Radnički Niš | - | Proleter Novi Sad | 3:0 |  |
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| 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 |  |
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| 8. Round | 13/09/2019 | Radnički Niš | - | Vojvodina | 1:2 |
Montenegro