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| 12/10/2018 | 19:35 | Arbroath FC | - | Edinburgh City FC | 1:4 (1:1) | |
| 13/10/2018 | 15:00 | East Fife FC | - | Queen Of The South | 2:0 (1:0) | |
| 15:00 | Bohemian FC | - | Sutton United | 4:3 (0:0, 0:0) pso | ||
| 15:00 | Dunfermline Athletic | - | Alloa Athletic | 4:5 (1:1, 2:2) pso | ||
| 15:00 | Ross County FC | - | Montrose FC | 3:1 (2:1) | ||
| 15:00 | St. Mirren FC (R) | - | Queen's Park FC | 2:4 (1:0) | ||
| 15:00 | Motherwell FC (R) | - | Sligo Rovers | 2:0 (1:0) | ||
| 19:30 | Connah's Quay Nomads | - | Coleraine FC | 2:0 (0:0) |
