1. Round | 05/08/2023 | Greenock Morton FC | - | Ayr United | 3:1 | ||||
9. Round | 21/10/2023 | Dunfermline Athletic | - | Ayr United | 0:1 | ||||
10. Round | 28/10/2023 | Ayr United | - | Greenock Morton FC | 0:1 | ||||
11. Round | 31/10/2023 | Partick Thistle | - | Ayr United | 2:2 | ||||
12. Round | 04/11/2023 | Ayr United | - | Queen's Park FC | 2:2 | ||||
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 | ||||
20. Round | 06/01/2024 | Ayr United | - | Inverness CT | 1:3 | ||||
21. Round | 13/01/2024 | Arbroath FC | - | Ayr United | 0:0 |