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| 22/11/2019 | 19:05 | Linlithgow Rose | - | Falkirk FC | 1:4 (1:2) | |
| 23/11/2019 | 13:45 | Auchinleck Talbot | - | Arbroath FC | 1:1 (1:0) | |
| 15:00 | Albion Rovers | - | Airdrieonians FC | 1:4 (0:1) | ||
| 15:00 | Bonnyrigg Rose Athletic | - | Montrose FC | 2:1 (2:1) | ||
| 15:00 | Dumbarton FC | - | Forfar Athletic | 3:1 (1:1) | ||
| 15:00 | East Fife FC | - | BSC Glasgow | 3:4 (2:1) | ||
| 15:00 | Edinburgh City FC | - | Annan Athletic | 4:3 (3:0) | ||
| 15:00 | Elgin City | - | Alloa Athletic | 1:3 (1:0) | ||
| 15:00 | Formartine United | - | East Kilbride FC | 0:4 (0:1) | ||
| 15:00 | Greenock Morton FC | - | Brora Rangers FC | 1:1 (1:1) | ||
| 15:00 | Inverurie Loco Works | - | Broxburn Athletic | 0:1 (0:0) | ||
| 15:00 | Partick Thistle | - | Penicuik Athletic | 1:0 (1:0) | ||
| 15:00 | Queen Of The South | - | Queen's Park FC | 1:2 (0:2) | ||
| 15:00 | Raith Rovers | - | Peterhead FC | 1:0 (1:0) | ||
| 15:00 | Stirling Albion FC | - | Clyde FC | 0:2 (0:1) | ||
| 15:00 | Stranraer FC | - | Dunfermline Athletic | 1:0 (0:0) | ||
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 27/11/2019 | 19:45 | Arbroath FC | - | Auchinleck Talbot | 3:0 (1:0) | |
| 03/12/2019 | 19:45 | Brora Rangers FC | - | Greenock Morton FC | 1:3 (0:1) | |
