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| 05/09/2023 | 19:45 | Ayr United | - | Falkirk FC | 0:1 (0:1) | |
| 08/09/2023 | 18:00 | Hibernian FC (R) | - | The New Saints | 0:3 (0:2) | |
| 09/09/2023 | 13:00 | East Fife FC | - | Albion Rovers | 2:1 (0:1) | |
| 14:00 | Raith Rovers | - | Cliftonville FC | 3:0 (0:0) | ||
| 15:00 | Edinburgh City | - | East Kilbride FC | 1:4 (0:1) | ||
| 15:00 | Annan Athletic | - | Peterhead FC | 0:2 (0:1) | ||
| 15:00 | Cove Rangers | - | Montrose FC | 0:2 (0:0) | ||
| 15:00 | Dumbarton FC | - | Kelty Hearts | 1:3 (1:2) | ||
| 15:00 | University of Stirling FC | - | Airdrieonians FC | 2:3 (1:2) | ||
| 15:00 | Greenock Morton FC | - | Elgin City | 2:1 (1:1) | ||
| 15:00 | Dundee United | - | Dunfermline Athletic | 3:0 (3:0) | ||
| 15:00 | Arbroath FC | - | Inverness CT | 4:2 (2:1) | ||
| 15:00 | Partick Thistle | - | Queen Of The South | 2:3 (1:2) | ||
| 15:45 | Coleraine FC | - | Hamilton Academical | 1:3 (1:1) | ||
| 17:15 | Bala Town | - | Queen's Park FC | 0:3 (0:2) | ||
| 26/09/2023 | 19:45 | Rangers FC (R) | - | Alloa Athletic | 4:1 (1:1) |
