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| 19.01.2024 | 20:45 | Clyde FC | - | Aberdeen FC | 0:2 (0:1) | |
| 20.01.2024 | 13:15 | The Spartans FC | - | Heart of Midlothian | 1:2 (0:1) | |
| 16:00 | Airdrieonians FC | - | St. Johnstone FC | 1:0 (0:0) | ||
| 16:00 | Ayr United | - | Kelty Hearts | 3:0 (0:0) | ||
| 16:00 | Bonnyrigg Rose Athletic | - | Falkirk FC | 2:1 (1:1) | ||
| 16:00 | Forfar Athletic | - | Hibernian FC | 0:1 (0:0) | ||
| 16:00 | Greenock Morton FC | - | Montrose FC | 2:0 (1:0) | ||
| 16:00 | Inverness CT | - | Broomhill FC | 4:0 (1:0) | ||
| 16:00 | Kilmarnock FC | - | Dundee FC | 2:0 (2:0) | ||
| 16:00 | Livingston FC | - | Raith Rovers | 2:1 (1:1) | ||
| 16:00 | Motherwell FC | - | Alloa Athletic | 3:1 (1:1) | ||
| 16:00 | Ross County FC | - | Partick Thistle | 0:3 (0:2) | ||
| 16:00 | St. Mirren FC | - | Queen Of The South | 1:0 (0:0) | ||
| 18:30 | Dumbarton FC | - | Rangers FC | 1:4 (0:2) | ||
| 21.01.2024 | 17:00 | Celtic FC | - | Buckie Thistle | 5:0 (3:0) | |
| 30.01.2024 | 20:45 | Brora Rangers FC | - | Cove Rangers | 1:3 (1:1, 1:1) pró. |
