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 |