1. Round | 04/08/2018 | Ross County FC | - | Alloa Athletic | 1:0 | ||||
2. Round | 11/08/2018 | Alloa Athletic | - | Greenock Morton FC | 0:2 | ||||
3. Round | 25/08/2018 | Inverness CT | - | Alloa Athletic | 2:2 | ||||
5. Round | 15/09/2018 | Dunfermline Athletic | - | Alloa Athletic | 0:0 | ||||
6. Round | 22/09/2018 | Alloa Athletic | - | Ayr United | 0:2 | ||||
7. Round | 29/09/2018 | Alloa Athletic | - | Falkirk FC | 0:2 | ||||
11. Round | 30/10/2018 | Ayr United | - | Alloa Athletic | 3:0 | ||||
12. Round | 03/11/2018 | Alloa Athletic | - | Dunfermline Athletic | 0:1 | ||||
13. Round | 10/11/2018 | Greenock Morton FC | - | Alloa Athletic | 0:2 | ||||
15. Round | 01/12/2018 | Alloa Athletic | - | Ross County FC | 0:1 | ||||
16. Round | 08/12/2018 | Falkirk FC | - | Alloa Athletic | 2:2 | ||||
20. Round | 05/01/2019 | Dunfermline Athletic | - | Alloa Athletic | 2:2 | ||||
21. Round | 12/01/2019 | Alloa Athletic | - | Greenock Morton FC | 2:1 |