| 4. Round | 09/08/2019 | Crvena Zvezda | - | Mladost Lučani | 2:0 | ||||
| 5. Round | 17/08/2019 | Spartak Subotica | - | Crvena Zvezda | 2:3 | ||||
| 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 | ||||
| 11. Round | 06/10/2019 | FK Napredak | - | Crvena Zvezda | 0:1 | ||||
| 13. Round | 26/10/2019 | Radnik Surdulica | - | Crvena Zvezda | 0:5 |  |
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| 14. Round | 30/10/2019 | Crvena Zvezda | - | TSC Bačka Topola | 3:1 | ||||
| 15. Round | 02/11/2019 | Proleter Novi Sad | - | Crvena Zvezda | 0:2 | ||||
| 16. Round | 10/11/2019 | FK Javor | - | Crvena Zvezda | 1:1 | ||||
| 20. Round | 07/12/2019 | Crvena Zvezda | - | Spartak Subotica | 3:1 | ||||
| 6. Round | 15/12/2019 | Crvena Zvezda | - | FK Čukarički | 3:1 | |
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| 28. Round | 06/06/2020 | Crvena Zvezda | - | Radnik Surdulica | 4:1 | ||||
| 29. Round | 14/06/2020 | TSC Bačka Topola | - | Crvena Zvezda | 2:1 | ||||
| 30. Round | 20/06/2020 | Crvena Zvezda | - | Proleter Novi Sad | 2:1 |  |
Croatia