| 1. Round | 20/07/2019 | Crvena Zvezda | - | FK Javor | 2:0 | ||||
| 4. Round | 09/08/2019 | Crvena Zvezda | - | Mladost Lučani | 2:0 | ||||
| 9. Round | 22/09/2019 | Partizan | - | Crvena Zvezda | 2:0 |  |
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| 11. Round | 06/10/2019 | FK Napredak | - | Crvena Zvezda | 0:1 | ||||
| 15. Round | 02/11/2019 | Proleter Novi Sad | - | Crvena Zvezda | 0:2 |  |
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| 16. Round | 10/11/2019 | FK Javor | - | Crvena Zvezda | 1:1 | ||||
| 6. Round | 15/12/2019 | Crvena Zvezda | - | FK Čukarički | 3:1 | ||||
| 21. Round | 15/02/2020 | FK Čukarički | - | Crvena Zvezda | 0:2 | ||||
| 24. Round | 01/03/2020 | Crvena Zvezda | - | Partizan | 0:0 | ||||
| 28. Round | 06/06/2020 | Crvena Zvezda | - | Radnik Surdulica | 4:1 |
Ghana