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