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| 14/10/2023 | Raith Rovers | - | Montrose FC | -:- |
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| East Fife FC | - | Hamilton Academical | -:- | |||
| Falkirk FC | - | Queen's Park FC | -:- |
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| Queen Of The South | - | Arbroath FC | -:- |
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| Greenock Morton FC | - | Kelty Hearts | -:- |
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| Rangers FC (R) | - | Airdrieonians FC | -:- | |||
| 17:15 | The New Saints | - | East Fife FC | -:- |
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| 17:30 | Peterhead FC | - | Dundee United | -:- |
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