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| 1st(1st leg) | NK Aluminij | - | FC Koper | 1:0 (0:0) | ||
| 2nd (2nd leg) | FC Koper | - | NK Aluminij | 3:2 (2:1) | ||
| 1st(1st leg): 16/10/2019 16:00 | 2nd (2nd leg): 29/10/2019 15:30 | Winner: NK Aluminij | ||||
| 1st(1st leg) | NK Nafta | - | Rudar Velenje | 2:1 (0:0) | ||
| 2nd (2nd leg) | Rudar Velenje | - | NK Nafta | 0:2 (0:1) | ||
| 1st(1st leg): 16/10/2019 18:00 | 2nd (2nd leg): 30/10/2019 15:30 | Winner: NK Nafta | ||||
| 1st(1st leg) | NK Celje | - | NK Radomlje | 1:1 (1:0) | ||
| 2nd (2nd leg) | NK Radomlje | - | NK Celje | 0:0 (0:0) | ||
| 1st(1st leg): 22/10/2019 16:00 | 2nd (2nd leg): 29/10/2019 12:30 | Winner: NK Radomlje | ||||
| 1st(1st leg) | NK Domžale | - | NŠ Mura | 3:2 (1:1) | ||
| 2nd (2nd leg) | NŠ Mura | - | NK Domžale | 5:4 (1:2, 3:2, 3:2) pso | ||
| 1st(1st leg): 24/10/2019 16:00 | 2nd (2nd leg): 30/10/2019 18:30 | Winner: NŠ Mura | ||||
