| 2. Round | 27/07/2019 | Crvena Zvezda | - | Radnički Niš | 2:0 | ||||
| 7. Round | 31/08/2019 | Vojvodina | - | Crvena Zvezda | 1:2 | ||||
| 8. Round | 14/09/2019 | Crvena Zvezda | - | FK Inđija | 2:1 | ||||
| 3. Round | 25/09/2019 | FK Voždovac | - | Crvena Zvezda | 1:3 | ||||
| 10. Round | 28/09/2019 | Crvena Zvezda | - | Mačva Šabac | 3:1 |  |
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| 13. Round | 26/10/2019 | Radnik Surdulica | - | Crvena Zvezda | 0:5 | ||||
| 15. Round | 02/11/2019 | Proleter Novi Sad | - | Crvena Zvezda | 0:2 | ||||
| 16. Round | 10/11/2019 | FK Javor | - | Crvena Zvezda | 1:1 | ||||
| 17. Round | 23/11/2019 | Radnički Niš | - | Crvena Zvezda | 0:2 |
Spain
