1. Round | 03/08/2019 | Ayr United | - | Greenock Morton FC | 4:2 | ||||
2. Round | 10/08/2019 | Dundee FC | - | Ayr United | 1:0 | ||||
3. Round | 24/08/2019 | Ayr United | - | Queen Of The South | 1:0 | ||||
4. Round | 31/08/2019 | Partick Thistle | - | Ayr United | 2:3 | ||||
15. Round | 10/12/2019 | Ayr United | - | Arbroath FC | 1:1 | ||||
17. Round | 14/12/2019 | Ayr United | - | Alloa Athletic | 2:1 | ||||
18. Round | 21/12/2019 | Dundee United | - | Ayr United | 4:0 | ||||
19. Round | 28/12/2019 | Ayr United | - | Queen Of The South | 1:2 | ||||
20. Round | 04/01/2020 | Dunfermline Athletic | - | Ayr United | 0:1 | ||||
22. Round | 25/01/2020 | Ayr United | - | Inverness CT | 1:0 | ||||
23. Round | 31/01/2020 | Partick Thistle | - | Ayr United | 1:1 | ||||
24. Round | 25/02/2020 | Ayr United | - | Greenock Morton FC | 1:2 | ||||
26. Round | 29/02/2020 | Alloa Athletic | - | Ayr United | 0:2 | ||||
27. Round | 03/03/2020 | Ayr United | - | Dundee United | 0:0 | ||||
28. Round | 07/03/2020 | Ayr United | - | Dundee FC | 0:0 | ||||
21. Round | 10/03/2020 | Dundee FC | - | Ayr United | 2:0 |