| 2. Ronde | 10.08.2019 | Greenock Morton FC | - | Alloa Athletic | 4:1 | ||||
| 4. Ronde | 31.08.2019 | Queen Of The South | - | Alloa Athletic | 0:1 | ||||
| 6. Ronde | 21.09.2019 | Alloa Athletic | - | Ayr United | 1:4 | ||||
| 7. Ronde | 28.09.2019 | Dunfermline Athletic | - | Alloa Athletic | 1:1 |  |
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| 8. Ronde | 04.10.2019 | Alloa Athletic | - | Dundee United | 1:0 | ||||
| 9. Ronde | 19.10.2019 | Inverness CT | - | Alloa Athletic | 2:2 | ||||
| 10. Ronde | 26.10.2019 | Alloa Athletic | - | Queen Of The South | 2:2 | ||||
| 11. Ronde | 29.10.2019 | Alloa Athletic | - | Dundee FC | 0:3 | ||||
| 12. Ronde | 02.11.2019 | Arbroath FC | - | Alloa Athletic | 2:1 | ||||
| 13. Ronde | 09.11.2019 | Alloa Athletic | - | Dunfermline Athletic | 2:1 | ||||
| 17. Ronde | 14.12.2019 | Ayr United | - | Alloa Athletic | 2:1 | ||||
| 19. Ronde | 28.12.2019 | Dunfermline Athletic | - | Alloa Athletic | 1:3 | |
 |
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| 20. Ronde | 04.01.2020 | Alloa Athletic | - | Partick Thistle | 1:1 | |
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| 28. Ronde | 07.03.2020 | Alloa Athletic | - | Inverness CT | 2:0 |
Schotland