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| 17.01.2020 | 20:45 | Rangers FC | - | Stranraer FC | 2:0 (1:0) | |
| 18.01.2020 | 16:00 | St. Mirren FC | - | Broxburn Athletic | 3:0 (0:0) | |
| 16:00 | Kilmarnock FC | - | Queen's Park FC | 6:0 (3:0) | ||
| 16:00 | Heart of Midlothian | - | Airdrieonians FC | 5:0 (1:0) | ||
| 16:00 | Alloa Athletic | - | Inverness CT | 2:3 (1:1) | ||
| 16:00 | Livingston FC | - | Raith Rovers | 3:1 (0:1) | ||
| 16:00 | Arbroath FC | - | Falkirk FC | 0:0 (0:0) | ||
| 16:00 | Ayr United | - | Ross County FC | 1:0 (1:0) | ||
| 16:00 | Aberdeen FC | - | Dumbarton FC | 1:0 (0:0) | ||
| 16:00 | Bonnyrigg Rose Athletic | - | Clyde FC | 0:1 (0:0) | ||
| 16:00 | St. Johnstone FC | - | Greenock Morton FC | 3:0 (1:0) | ||
| 16:00 | Hamilton Academical | - | Edinburgh City FC | 5:0 (3:0) | ||
| 16:00 | East Kilbride FC | - | BSC Glasgow | 1:3 (0:3) | ||
| 18:30 | Partick Thistle | - | Celtic FC | 1:2 (0:1) | ||
| 20:20 | Dundee FC | - | Motherwell FC | 0:3 (0:2) | ||
| 19.01.2020 | 16:00 | Dundee United | - | Hibernian FC | 2:2 (1:1) | |
| Entscheidungsspiele | ||||||
|---|---|---|---|---|---|---|
| 28.01.2020 | 20:45 | Falkirk FC | - | Arbroath FC | 2:0 (0:0) | |
| 20:45 | Hibernian FC | - | Dundee United | 4:2 (1:1) | ||
