| 23. Round | 03/02/2024 | Ayr United | - | Dundee United | 1:2 | ||||
| 25. Round | 24/02/2024 | Ayr United | - | Raith Rovers | 1:2 | ||||
| 26. Round | 27/02/2024 | Ayr United | - | Partick Thistle | 4:3 |  |
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| 27. Round | 02/03/2024 | Dunfermline Athletic | - | Ayr United | 2:0 | ||||
| 29. Round | 16/03/2024 | Inverness CT | - | Ayr United | 1:2 | ||||
| 30. Round | 23/03/2024 | Ayr United | - | Queen's Park FC | 1:2 | ||||
| 31. Round | 29/03/2024 | Ayr United | - | Airdrieonians FC | 2:1 | ||||
| 32. Round | 06/04/2024 | Raith Rovers | - | Ayr United | 2:1 | ||||
| 33. Round | 13/04/2024 | Ayr United | - | Arbroath FC | 5:0 | ||||
| 34. Round | 20/04/2024 | Dundee United | - | Ayr United | 1:0 | |
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| 35. Round | 27/04/2024 | Partick Thistle | - | Ayr United | 0:0 | ||||
| 36. Round | 03/05/2024 | Ayr United | - | Dunfermline Athletic | 3:3 |
England