| 3. Jornada | 24.08.2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
| 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 | ||||
| 16. Jornada | 07.12.2019 | Dundee United | - | Alloa Athletic | 2:1 | ||||
| 15. Jornada | 10.12.2019 | Greenock Morton FC | - | Dundee United | 1:2 | ||||
| 18. Jornada | 21.12.2019 | Dundee United | - | Ayr United | 4:0 | ||||
| 20. Jornada | 04.01.2020 | Queen Of The South | - | Dundee United | 0:1 |  |
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| 21. Jornada | 11.01.2020 | Partick Thistle | - | Dundee United | 1:4 |
Escocia