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| 1st(1st leg) | FK Belasica | - | Makedonija GP | 0:1 (0:1) | ||
| 2nd (2nd leg) | Makedonija GP | - | FK Belasica | 1:0 (0:0) | ||
| 1st(1st leg): 27/02/2019 13:00 | 2nd (2nd leg): 10/04/2019 14:30 | Winner: Makedonija GP | ||||
| 1st(1st leg) | Akademija Pandev | - | FK Pobeda | 3:1 (0:0) | ||
| 2nd (2nd leg) | FK Pobeda | - | Akademija Pandev | 1:3 (1:0) | ||
| 1st(1st leg): 06/03/2019 13:00 | 2nd (2nd leg): 10/04/2019 14:30 | Winner: Akademija Pandev | ||||
