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 | ||||
6. Round | 21/09/2019 | Alloa Athletic | - | Ayr United | 1:4 | ||||
7. Round | 28/09/2019 | Arbroath FC | - | Ayr United | 0:3 | ||||
8. Round | 05/10/2019 | Ayr United | - | Inverness CT | 0:2 | ||||
9. Round | 19/10/2019 | Dunfermline Athletic | - | Ayr United | 3:2 | ||||
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 |