1. Round | 10/08/2019 | FC Struga | - | FK Rabotnički | 2:1 | ||||
2. Round | 17/08/2019 | FK Rabotnički | - | KF Shkupi | 2:0 | ||||
13. Round | 02/11/2019 | Akademija Pandev | - | FK Rabotnički | 1:1 | ||||
15. Round | 23/11/2019 | Makedonija GP | - | FK Rabotnički | 2:0 | ||||
16. Round | 27/11/2019 | FK Rabotnički | - | FK Borec | 2:1 | ||||
17. Round | 01/12/2019 | FK Rabotnički | - | Sileks Kratovo | 1:1 | ||||
18. Round | 08/12/2019 | FK Renova | - | FK Rabotnički | 4:3 |