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| 11/09/2019 | 14:30 | NK Tolmin | - | NK Celje | 0:6 (0:2) | |
| 14:30 | NK Radomlje | - | ND Gorica | 3:2 (2:2, 2:2) aet | ||
| 17:00 | NK Nafta | - | NK Krško | 2:0 (1:0) | ||
| 18/09/2019 | 14:30 | NK Triglav | - | NŠ Mura | 1:3 (0:3) | |
| 14:30 | NK Brda | - | NK Domžale | 0:3 (0:1) | ||
| 15:30 | FC Koper | - | NK Maribor | 3:2 (1:1) | ||
| 16:00 | NK Aluminij | - | NK Tabor Sežana | 1:0 (0:0) | ||
| 19/09/2019 | 15:30 | Olimpija Ljubljana | - | Rudar Velenje | 0:1 (0:0) |
