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 | ||||
4. Round | 01/09/2018 | Alloa Athletic | - | Dundee United | 1:1 | ||||
7. Round | 29/09/2018 | Alloa Athletic | - | Falkirk FC | 0:2 | ||||
8. Round | 06/10/2018 | Queen Of The South | - | Alloa Athletic | 3:3 | ||||
9. Round | 20/10/2018 | Alloa Athletic | - | Partick Thistle | 1:0 | ||||
10. Round | 27/10/2018 | Alloa Athletic | - | Inverness CT | 0:0 | ||||
12. Round | 03/11/2018 | Alloa Athletic | - | Dunfermline Athletic | 0:1 | ||||
18. Round | 22/12/2018 | Alloa Athletic | - | Queen Of The South | 2:0 | ||||
19. Round | 29/12/2018 | Alloa Athletic | - | Dundee United | 2:1 | ||||
30. Round | 23/03/2019 | Dundee United | - | Alloa Athletic | 2:1 | ||||
27. Round | 26/03/2019 | Inverness CT | - | Alloa Athletic | 3:2 | ||||
36. Round | 04/05/2019 | Ayr United | - | Alloa Athletic | 1:1 |