| 1. Jornada | 03.08.2019 | Ayr United | - | Greenock Morton FC | 4:2 | ||||
| 3. Jornada | 23.08.2019 | Greenock Morton FC | - | Partick Thistle | 3:2 | ||||
| 6. Jornada | 21.09.2019 | Greenock Morton FC | - | Dundee FC | 1:0 |  |
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| 7. Jornada | 28.09.2019 | Dundee United | - | Greenock Morton FC | 6:0 | ||||
| 8. Jornada | 05.10.2019 | Greenock Morton FC | - | Dunfermline Athletic | 1:1 |  |
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| 9. Jornada | 19.10.2019 | Arbroath FC | - | Greenock Morton FC | 1:0 | ||||
| 10. Jornada | 26.10.2019 | Greenock Morton FC | - | Inverness CT | 2:1 | ||||
| 11. Jornada | 29.10.2019 | Greenock Morton FC | - | Ayr United | 2:3 | ||||
| 12. Jornada | 01.11.2019 | Dundee FC | - | Greenock Morton FC | 2:1 | ||||
| 13. Jornada | 09.11.2019 | Partick Thistle | - | Greenock Morton FC | 2:1 | ||||
| 14. Jornada | 16.11.2019 | Greenock Morton FC | - | Arbroath FC | 1:0 | ||||
| 16. Jornada | 07.12.2019 | Dunfermline Athletic | - | Greenock Morton FC | 3:1 | |
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| 15. Jornada | 10.12.2019 | Greenock Morton FC | - | Dundee United | 1:2 | ||||
| 18. Jornada | 21.12.2019 | Alloa Athletic | - | Greenock Morton FC | 0:2 | ||||
| 19. Jornada | 28.12.2019 | Greenock Morton FC | - | Partick Thistle | 1:2 | ||||
| 20. Jornada | 04.01.2020 | Arbroath FC | - | Greenock Morton FC | 1:2 |
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