| 1. Jornada | 03.08.2019 | Dundee United | - | Inverness CT | 4:1 | ||||
| 3. Jornada | 24.08.2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
| 4. Jornada | 30.08.2019 | Dundee United | - | Dundee FC | 6:2 |  |
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| 5. Jornada | 14.09.2019 | Ayr United | - | Dundee United | 2:0 | ||||
| 6. Jornada | 21.09.2019 | Dundee United | - | Arbroath FC | 2:1 | ||||
| 8. Jornada | 04.10.2019 | Alloa Athletic | - | Dundee United | 1:0 | ||||
| 10. Jornada | 26.10.2019 | Dundee United | - | Dunfermline Athletic | 2:0 | ||||
| 12. Jornada | 02.11.2019 | Inverness CT | - | Dundee United | 0:3 | ||||
| 13. Jornada | 08.11.2019 | Dundee FC | - | Dundee United | 0:2 | ||||
| 14. Jornada | 16.11.2019 | Dundee United | - | Queen Of The South | 3:0 | ||||
| 20. Jornada | 04.01.2020 | Queen Of The South | - | Dundee United | 0:1 |
Escocia