| 1. Round | 20/07/2018 | Crvena Zvezda | - | Dinamo Vranje | 3:0 |  |
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| 2. Round | 29/07/2018 | Crvena Zvezda | - | Radnički Niš | 2:0 | ||||
| 3. Round | 04/08/2018 | FK Voždovac | - | Crvena Zvezda | 1:2 | ||||
| 4. Round | 12/08/2018 | Crvena Zvezda | - | Spartak Subotica | 3:0 | ||||
| 6. Round | 25/08/2018 | Crvena Zvezda | - | FK Čukarički | 2:1 | ||||
| 5. Round | 26/09/2018 | FK Napredak | - | Crvena Zvezda | 0:3 | |
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| 14. Round | 31/10/2018 | Crvena Zvezda | - | OFK Bačka | 3:1 | ||||
| 21. Round | 16/12/2018 | FK Čukarički | - | Crvena Zvezda | 1:2 |
Serbia