| 1. Journée | 03.08.2019 | Ayr United | - | Greenock Morton FC | 4:2 | ||||
| 2. Journée | 10.08.2019 | Greenock Morton FC | - | Alloa Athletic | 4:1 | ||||
| 4. Journée | 30.08.2019 | Inverness CT | - | Greenock Morton FC | 5:0 |  |
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| 5. Journée | 14.09.2019 | Queen Of The South | - | Greenock Morton FC | 1:0 | |
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| 6. Journée | 21.09.2019 | Greenock Morton FC | - | Dundee FC | 1:0 | ||||
| 8. Journée | 05.10.2019 | Greenock Morton FC | - | Dunfermline Athletic | 1:1 | ||||
| 10. Journée | 26.10.2019 | Greenock Morton FC | - | Inverness CT | 2:1 | ||||
| 11. Journée | 29.10.2019 | Greenock Morton FC | - | Ayr United | 2:3 | |
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| 12. Journée | 01.11.2019 | Dundee FC | - | Greenock Morton FC | 2:1 |  |
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| 13. Journée | 09.11.2019 | Partick Thistle | - | Greenock Morton FC | 2:1 | ||||
| 14. Journée | 16.11.2019 | Greenock Morton FC | - | Arbroath FC | 1:0 | ||||
| 16. Journée | 07.12.2019 | Dunfermline Athletic | - | Greenock Morton FC | 3:1 | ||||
| 15. Journée | 10.12.2019 | Greenock Morton FC | - | Dundee United | 1:2 |
Angleterre