| 4. Round | 14/09/2008 | FK Čukarički | - | Crvena Zvezda | 2:2 |  |
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| 6. Round | 27/09/2008 | Hajduk Rodić | - | Crvena Zvezda | 1:2 | ||||
| 8. Round | 19/10/2008 | FK Napredak | - | Crvena Zvezda | 1:2 |  |
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| 9. Round | 25/10/2008 | Crvena Zvezda | - | OFK Beograd | 5:1 | ||||
| 11. Round | 01/11/2008 | Crvena Zvezda | - | FK Rad Beograd | 2:0 | |
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| 12. Round | 08/11/2008 | Crvena Zvezda | - | Vojvodina | 3:1 | |
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| 13. Round | 15/11/2008 | Crvena Zvezda | - | FK Banat Zrenjanin | 2:1 | ||||
| 14. Round | 23/11/2008 | FK Javor | - | Crvena Zvezda | 1:1 | ||||
| 15. Round | 29/11/2008 | Crvena Zvezda | - | FK Čukarički | 2:0 | ||||
| 17. Round | 10/12/2008 | Crvena Zvezda | - | Hajduk Rodić | 1:2 | ||||
| 19. Round | 07/03/2009 | Crvena Zvezda | - | FK Napredak | 4:0 | |
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| 20. Round | 14/03/2009 | OFK Beograd | - | Crvena Zvezda | 2:2 | ||||
| 23. Round | 04/04/2009 | Crvena Zvezda | - | FK Čukarički | 2:1 | ||||
| 25. Round | 11/04/2009 | Crvena Zvezda | - | FK Banat Zrenjanin | 3:0 |
North Macedonia