1. Round | 20/07/2018 | Crvena Zvezda | - | Dinamo Vranje | 3:0 | ||||
3. Round | 04/08/2018 | FK Voždovac | - | Crvena Zvezda | 1:2 | ||||
4. Round | 12/08/2018 | Crvena Zvezda | - | Spartak Subotica | 3:0 | ||||
16. Round | 10/11/2018 | Dinamo Vranje | - | Crvena Zvezda | 0:3 | ||||
17. Round | 24/11/2018 | Radnički Niš | - | Crvena Zvezda | 2:2 | ||||
30. Round | 07/04/2019 | Crvena Zvezda | - | Proleter Novi Sad | 4:0 |