| 1. Jornada | 04.08.2018 | Dundee United | - | Dunfermline Athletic | 2:3 | ||||
| 2. Jornada | 11.08.2018 | Queen Of The South | - | Dundee United | 1:2 | ||||
| 3. Jornada | 25.08.2018 | Dundee United | - | Partick Thistle | 3:1 |  |
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| 4. Jornada | 01.09.2018 | Alloa Athletic | - | Dundee United | 1:1 |  |
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| 5. Jornada | 15.09.2018 | Dundee United | - | Greenock Morton FC | 1:1 | ||||
| 6. Jornada | 22.09.2018 | Falkirk FC | - | Dundee United | 0:2 | |
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| 7. Jornada | 29.09.2018 | Dundee United | - | Ross County FC | 1:5 | |
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| 11. Jornada | 13.10.2018 | Partick Thistle | - | Dundee United | 1:2 | |
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| 10. Jornada | 27.10.2018 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
| 12. Jornada | 03.11.2018 | Dundee United | - | Queen Of The South | 2:0 | ||||
| 14. Jornada | 20.11.2018 | Dundee United | - | Alloa Athletic | 4:2 | |
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| 15. Jornada | 30.11.2018 | Dundee United | - | Ayr United | 0:5 | ||||
| 16. Jornada | 08.12.2018 | Greenock Morton FC | - | Dundee United | 1:1 | ||||
| 17. Jornada | 15.12.2018 | Inverness CT | - | Dundee United | 1:1 | ||||
| 18. Jornada | 22.12.2018 | Dundee United | - | Falkirk FC | 2:1 | |
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| 19. Jornada | 29.12.2018 | Alloa Athletic | - | Dundee United | 2:1 |
Inglaterra