| 2. Round | 10/08/2019 | Greenock Morton FC | - | Alloa Athletic | 4:1 | ||||
| 4. Round | 31/08/2019 | Queen Of The South | - | Alloa Athletic | 0:1 | ||||
| 6. Round | 21/09/2019 | Alloa Athletic | - | Ayr United | 1:4 | ||||
| 7. Round | 28/09/2019 | Dunfermline Athletic | - | Alloa Athletic | 1:1 |  |
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| 8. Round | 04/10/2019 | Alloa Athletic | - | Dundee United | 1:0 | ||||
| 9. Round | 19/10/2019 | Inverness CT | - | Alloa Athletic | 2:2 | ||||
| 10. Round | 26/10/2019 | Alloa Athletic | - | Queen Of The South | 2:2 | ||||
| 11. Round | 29/10/2019 | Alloa Athletic | - | Dundee FC | 0:3 | ||||
| 12. Round | 02/11/2019 | Arbroath FC | - | Alloa Athletic | 2:1 | ||||
| 13. Round | 09/11/2019 | Alloa Athletic | - | Dunfermline Athletic | 2:1 | ||||
| 17. Round | 14/12/2019 | Ayr United | - | Alloa Athletic | 2:1 | ||||
| 19. Round | 28/12/2019 | Dunfermline Athletic | - | Alloa Athletic | 1:3 | |
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| 20. Round | 04/01/2020 | Alloa Athletic | - | Partick Thistle | 1:1 | |
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| 28. Round | 07/03/2020 | Alloa Athletic | - | Inverness CT | 2:0 |
Scotland