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| 24/11/2018 | 13:30 | Beith Juniors FC | - | Ayr United | 0:3 (0:0) | |
| 15:00 | Airdrieonians FC | - | Dumbarton FC | 3:0 (2:0) | ||
| 15:00 | Alloa Athletic | - | Brechin City FC | 3:0 (1:0) | ||
| 15:00 | Arbroath FC | - | Stranraer FC | 0:1 (0:0) | ||
| 15:00 | Berwick Rangers | - | East Fife FC | 1:2 (0:2) | ||
| 15:00 | Cowdenbeath FC | - | Brora Rangers FC | 1:0 (1:0) | ||
| 15:00 | East Kilbride FC | - | Gala Fairydean Rovers | 1:0 (0:0) | ||
| 15:00 | Forfar Athletic | - | BSC Glasgow | 2:0 (0:0) | ||
| 15:00 | Fraserburgh FC | - | Auchinleck Talbot | 0:1 (0:0) | ||
| 15:00 | Greenock Morton FC | - | Peterhead FC | 1:1 (1:1) | ||
| 15:00 | Montrose FC | - | Annan Athletic | 0:0 (0:0) | ||
| 15:00 | Queen Of The South | - | Formartine United | 4:1 (3:1) | ||
| 15:00 | Queen's Park FC | - | Raith Rovers | 0:3 (0:2) | ||
| 15:00 | Stenhousemuir FC | - | Falkirk FC | 4:2 (2:2) | ||
| 15:00 | University of Stirling FC | - | Elgin City | 0:4 (0:2) | ||
| 25/11/2018 | 15:00 | Edinburgh City FC | - | Inverness CT | 1:1 (0:1) | |
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 27/11/2018 | 19:45 | Annan Athletic | - | Montrose FC | 3:4 (0:4) | |
| 19:45 | Peterhead FC | - | Greenock Morton FC | 0:3 (0:1) | ||
| 04/12/2018 | 19:45 | Inverness CT | - | Edinburgh City FC | 6:1 (2:1) | |
