1. Round | 17/08/2008 | Vojvodina | - | Crvena Zvezda | 2:0 | ||||
2. Round | 23/08/2008 | FK Banat Zrenjanin | - | Crvena Zvezda | 0:0 | ||||
3. Round | 31/08/2008 | Crvena Zvezda | - | FK Javor | 0:2 | ||||
4. Round | 14/09/2008 | FK Čukarički | - | Crvena Zvezda | 2:2 | ||||
5. Round | 20/09/2008 | Crvena Zvezda | - | FK Jagodina | 3:0 | ||||
6. Round | 27/09/2008 | Hajduk Rodić | - | Crvena Zvezda | 1:2 | ||||
7. Round | 05/10/2008 | Crvena Zvezda | - | Partizan | 0:2 | ||||
17. Round | 10/12/2008 | Crvena Zvezda | - | Hajduk Rodić | 1:2 |