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| 06.09.2018 | 20:00 | Dundee FC (R) | - | Motherwell FC (R) | 1:2 (1:1) | |
| 08.09.2018 | 14:00 | Boreham Wood | - | Dunfermline Athletic | 5:6 (0:0, 0:0) i.E. | |
| 15:30 | Queen Of The South | - | Crusaders FC | 4:3 (4:0) | ||
| 16:00 | Falkirk FC | - | Connah's Quay Nomads | 0:1 (0:0) | ||
| 16:00 | Airdrieonians FC | - | Sutton United | 0:1 (0:1) | ||
| 16:00 | Peterhead FC | - | Bohemian FC | 0:1 (0:0) | ||
| 16:00 | East Fife FC | - | Partick Thistle | 2:1 (0:1) | ||
| 16:00 | Arbroath FC | - | Annan Athletic | 3:0 (1:0) | ||
| 16:00 | Dumbarton FC | - | Montrose FC | 0:1 (0:1) | ||
| 16:00 | Dundee United | - | Alloa Athletic | 4:5 (1:0, 1:1) i.E. | ||
| 16:00 | East Kilbride FC | - | Edinburgh City FC | 2:3 (0:1) | ||
| 16:00 | St. Mirren FC (R) | - | Hamilton Academical (R) | 3:2 (2:1) | ||
| 16:00 | Ross County FC | - | Raith Rovers | 5:0 (5:0) | ||
| 20:35 | The New Saints | - | Queen's Park FC | 2:4 (1:0, 2:2) i.E. | ||
| 20:45 | Coleraine FC | - | Formartine United | 2:1 (1:1, 1:1) i.E. | ||
| 20:45 | Sligo Rovers | - | Livingston FC (R) | 4:1 (1:1) |
