| 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 |
Scotland