| 1. Round | 05/08/2023 | Dunfermline Athletic | - | Airdrieonians FC | 2:1 | ||||
| 2. Round | 12/08/2023 | Airdrieonians FC | - | Partick Thistle | 2:1 | ||||
| 5. Round | 16/09/2023 | Arbroath FC | - | Airdrieonians FC | 4:0 |  |
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| 10. Round | 28/10/2023 | Inverness CT | - | Airdrieonians FC | 1:0 | ||||
| 12. Round | 04/11/2023 | Raith Rovers | - | Airdrieonians FC | 1:1 | ||||
| 13. Round | 11/11/2023 | Airdrieonians FC | - | Arbroath FC | 2:0 | ||||
| 16. Round | 16/12/2023 | Ayr United | - | Airdrieonians FC | 1:0 | |
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| 17. Round | 23/12/2023 | Airdrieonians FC | - | Greenock Morton FC | 0:0 | ||||
| 18. Round | 30/12/2023 | Queen's Park FC | - | Airdrieonians FC | 1:2 | ||||
| 19. Round | 02/01/2024 | Airdrieonians FC | - | Inverness CT | 2:0 | ||||
| 20. Round | 06/01/2024 | Airdrieonians FC | - | Raith Rovers | 1:0 | ||||
| 22. Round | 27/01/2024 | Airdrieonians FC | - | Partick Thistle | 1:1 | ||||
| 24. Round | 17/02/2024 | Airdrieonians FC | - | Ayr United | 2:3 | ||||
| 26. Round | 27/02/2024 | Dundee United | - | Airdrieonians FC | 0:2 | ||||
| 21. Round | 05/03/2024 | Dunfermline Athletic | - | Airdrieonians FC | 0:2 | |
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| 28. Round | 09/03/2024 | Inverness CT | - | Airdrieonians FC | 0:0 | |
Scotland