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 | ||||
10. Round | 25/10/2019 | Ayr United | - | Dundee FC | 1:2 | ||||
11. Round | 29/10/2019 | Greenock Morton FC | - | Ayr United | 2:3 | ||||
12. Round | 02/11/2019 | Ayr United | - | Partick Thistle | 4:1 | ||||
14. Round | 03/12/2019 | Ayr United | - | Dunfermline Athletic | 0:1 | ||||
16. Round | 07/12/2019 | Inverness CT | - | Ayr United | 2:0 | ||||
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 |