3. Round | 25/08/2018 | Inverness CT | - | Alloa Athletic | 2:2 | ||||
4. Round | 01/09/2018 | Alloa Athletic | - | Dundee United | 1:1 | ||||
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 | ||||
8. Round | 06/10/2018 | Queen Of The South | - | Alloa Athletic | 3:3 | ||||
11. Round | 30/10/2018 | Ayr United | - | Alloa Athletic | 3:0 | ||||
18. Round | 22/12/2018 | Alloa Athletic | - | Queen Of The South | 2:0 | ||||
20. Round | 05/01/2019 | Dunfermline Athletic | - | Alloa Athletic | 2:2 |