| 2. Jornada | 09.08.2019 | Partick Thistle | - | Dundee United | 1:2 |  |
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| 3. Jornada | 24.08.2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
| 4. Jornada | 30.08.2019 | Dundee United | - | Dundee FC | 6:2 | ||||
| 5. Jornada | 14.09.2019 | Ayr United | - | Dundee United | 2:0 | ||||
| 6. Jornada | 21.09.2019 | Dundee United | - | Arbroath FC | 2:1 | ||||
| 7. Jornada | 28.09.2019 | Dundee United | - | Greenock Morton FC | 6:0 | ||||
| 8. Jornada | 04.10.2019 | Alloa Athletic | - | Dundee United | 1:0 | ||||
| 10. Jornada | 26.10.2019 | Dundee United | - | Dunfermline Athletic | 2:0 | ||||
| 11. Jornada | 29.10.2019 | Dundee United | - | Partick Thistle | 1:0 | ||||
| 21. Jornada | 11.01.2020 | Partick Thistle | - | Dundee United | 1:4 | ||||
| 22. Jornada | 25.01.2020 | Dundee United | - | Greenock Morton FC | 1:1 | ||||
| 23. Jornada | 01.02.2020 | Dundee United | - | Arbroath FC | 0:1 |  |
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| 24. Jornada | 14.02.2020 | Alloa Athletic | - | Dundee United | 0:0 | ||||
| 25. Jornada | 21.02.2020 | Dundee United | - | Inverness CT | 2:1 | ||||
| 26. Jornada | 29.02.2020 | Dunfermline Athletic | - | Dundee United | 2:0 | ||||
| 27. Jornada | 03.03.2020 | Ayr United | - | Dundee United | 0:0 | ||||
| 28. Jornada | 07.03.2020 | Dundee United | - | Partick Thistle | 1:1 |
Inglaterra