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