| 1. Jornada | 04.08.2018 | Ross County FC | - | Alloa Athletic | 1:0 | ||||
| 2. Jornada | 11.08.2018 | Alloa Athletic | - | Greenock Morton FC | 0:2 | ||||
| 3. Jornada | 25.08.2018 | Inverness CT | - | Alloa Athletic | 2:2 | ||||
| 5. Jornada | 15.09.2018 | Dunfermline Athletic | - | Alloa Athletic | 0:0 | ||||
| 6. Jornada | 22.09.2018 | Alloa Athletic | - | Ayr United | 0:2 | ||||
| 7. Jornada | 29.09.2018 | Alloa Athletic | - | Falkirk FC | 0:2 | ||||
| 11. Jornada | 30.10.2018 | Ayr United | - | Alloa Athletic | 3:0 | ||||
| 12. Jornada | 03.11.2018 | Alloa Athletic | - | Dunfermline Athletic | 0:1 | ||||
| 13. Jornada | 10.11.2018 | Greenock Morton FC | - | Alloa Athletic | 0:2 | ||||
| 15. Jornada | 01.12.2018 | Alloa Athletic | - | Ross County FC | 0:1 | ||||
| 16. Jornada | 08.12.2018 | Falkirk FC | - | Alloa Athletic | 2:2 | ||||
| 20. Jornada | 05.01.2019 | Dunfermline Athletic | - | Alloa Athletic | 2:2 | ||||
| 21. Jornada | 12.01.2019 | Alloa Athletic | - | Greenock Morton FC | 2:1 |
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