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| 21.01.2023 | 13:15 | Celtic FC | - | Greenock Morton FC | 5:0 (4:0) | |
| 16:00 | Kilmarnock FC | - | Dumbarton FC | 1:0 (0:0) | ||
| 16:00 | Dundee United | - | University of Stirling FC | 3:0 (1:0) | ||
| 16:00 | St. Mirren FC | - | Dundee FC | 3:0 (0:0, 0:0, 0:0) d.p. | ||
| 16:00 | Partick Thistle | - | Dunfermline Athletic | 4:2 (0:1, 1:1, 1:1) d.p. | ||
| 16:00 | Arbroath FC | - | Motherwell FC | 0:2 (0:1) | ||
| 16:00 | Alloa Athletic | - | Falkirk FC | 1:2 (1:1) | ||
| 16:00 | Stenhousemuir FC | - | Livingston FC | 1:3 (1:0) | ||
| 16:00 | Hamilton Academical | - | Ross County FC | 5:3 (0:0, 0:0, 0:0) d.p. | ||
| 18:30 | St. Johnstone FC | - | Rangers FC | 0:1 (0:1) | ||
| 22.01.2023 | 15:00 | Hibernian FC | - | Heart of Midlothian | 0:3 (0:1) | |
| 23.01.2023 | 20:45 | Darvel FC | - | Aberdeen FC | 1:0 (1:0) | |
| 24.01.2023 | 20:45 | Elgin City | - | Drumchapel United | 2:1 (1:1) | |
| 20:45 | Linlithgow Rose | - | Raith Rovers | 0:2 (0:0) | ||
| 31.01.2023 | 20:45 | Inverness CT | - | Queen's Park FC | 0:2 (0:0) | |
| 20:45 | Cove Rangers | - | Ayr United | 0:3 (0:1) |
