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| 22.09.2022 | 20:45 | Greenock Morton FC | - | Ayr United | 5:4 (1:1, 1:1) pn. | |
| 20:45 | Queen Of The South | - | FC Edinburgh | 4:0 (1:0) | ||
| 23.09.2022 | 20:45 | Falkirk FC | - | Partick Thistle | 2:0 (1:0) | |
| 20:45 | Alloa Athletic | - | Airdrieonians FC | 1:0 (0:0) | ||
| 20:45 | Annan Athletic | - | Kelty Hearts | 1:2 (0:0) | ||
| 21:00 | The New Saints | - | Dundee FC | 0:3 (0:0) | ||
| 24.09.2022 | 15:00 | Inverness CT | - | Brechin City FC | 4:3 (2:1, 3:3) pn. | |
| 15:00 | Montrose FC | - | Kilmarnock FC (R) | 4:2 (1:0) | ||
| 16:00 | Buckie Thistle | - | Linfield FC | 1:2 (0:0) | ||
| 16:00 | Clyde FC | - | Caernarfon Town | 1:0 (0:0) | ||
| 16:00 | Peterhead FC | - | Elgin City | 0:4 (0:2) | ||
| 16:00 | Cove Rangers | - | Raith Rovers | 0:1 (0:1) | ||
| 16:00 | Arbroath FC | - | East Fife FC | 2:1 (2:0) | ||
| 25.09.2022 | 14:45 | Cliftonville FC | - | Queen's Park FC | 2:3 (1:2) | |
| 08.11.2022 | 20:45 | Rangers FC (R) | - | Hamilton Academical | 0:3 (0:1) | |
| 15.11.2022 | 20:45 | Dunfermline Athletic | - | Celtic FC (R) | 2:1 (2:1) |
