| 21. Round | 13/01/2024 | Arbroath FC | - | Ayr United | 0:0 | ||||
| 14. Round | 23/01/2024 | Ayr United | - | Arbroath FC | 2:0 |  |
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| 22. Round | 27/01/2024 | Greenock Morton FC | - | Arbroath FC | 3:0 | |
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| 24. Round | 17/02/2024 | Dunfermline Athletic | - | Arbroath FC | 1:1 | ||||
| 25. Round | 24/02/2024 | Arbroath FC | - | Inverness CT | 1:1 | ||||
| 26. Round | 27/02/2024 | Queen's Park FC | - | Arbroath FC | 6:0 | ||||
| 27. Round | 01/03/2024 | Arbroath FC | - | Raith Rovers | 3:2 | ||||
| 28. Round | 09/03/2024 | Dundee United | - | Arbroath FC | 4:0 |  |
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| 30. Round | 23/03/2024 | Arbroath FC | - | Partick Thistle | 0:1 | ||||
| 23. Round | 02/04/2024 | Arbroath FC | - | Airdrieonians FC | 1:2 |
Ireland