| 2. Round | 10/08/2019 | Queen Of The South | - | Dunfermline Athletic | 1:1 | ||||
| 3. Round | 24/08/2019 | Ayr United | - | Queen Of The South | 1:0 |  |
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| 4. Round | 31/08/2019 | Queen Of The South | - | Alloa Athletic | 0:1 | ||||
| 5. Round | 14/09/2019 | Queen Of The South | - | Greenock Morton FC | 1:0 |  |
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| 6. Round | 21/09/2019 | Inverness CT | - | Queen Of The South | 2:0 | |
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| 7. Round | 27/09/2019 | Queen Of The South | - | Dundee FC | 1:1 | |
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| 8. Round | 05/10/2019 | Partick Thistle | - | Queen Of The South | 0:1 | ||||
| 9. Round | 19/10/2019 | Queen Of The South | - | Dundee United | 4:0 | ||||
| 10. Round | 26/10/2019 | Alloa Athletic | - | Queen Of The South | 2:2 | ||||
| 11. Round | 29/10/2019 | Queen Of The South | - | Inverness CT | 0:2 | ||||
| 12. Round | 02/11/2019 | Dunfermline Athletic | - | Queen Of The South | 2:0 | ||||
| 15. Round | 30/11/2019 | Dundee FC | - | Queen Of The South | 1:2 | ||||
| 16. Round | 07/12/2019 | Queen Of The South | - | Partick Thistle | 1:2 | ||||
| 18. Round | 21/12/2019 | Queen Of The South | - | Arbroath FC | 2:0 | ||||
| 19. Round | 28/12/2019 | Ayr United | - | Queen Of The South | 1:2 | |
France