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| 14.10.2023 | 16:00 | Raith Rovers | - | Montrose FC | 3:1 (1:0) | |
| 16:00 | East Kilbride FC | - | Hamilton Academical | 2:5 (1:4) | ||
| 16:00 | Falkirk FC | - | Queen's Park FC | 1:0 (1:0) | ||
| 16:00 | Queen Of The South | - | Arbroath FC | 1:2 (1:0) | ||
| 16:00 | Greenock Morton FC | - | Kelty Hearts | 4:1 (1:1) | ||
| 18:15 | The New Saints | - | East Fife FC | 5:4 (1:1, 2:2) i.E. | ||
| 18:30 | Peterhead FC | - | Dundee United | 0:2 (0:1) | ||
| 07.11.2023 | 20:45 | Rangers FC (R) | - | Airdrieonians FC | 2:4 (1:2) |
