| 1. Round | 04/08/2018 | Dundee United | - | Dunfermline Athletic | 2:3 | ||||
| 2. Round | 11/08/2018 | Queen Of The South | - | Dundee United | 1:2 |  |
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| 3. Round | 25/08/2018 | Dundee United | - | Partick Thistle | 3:1 | ||||
| 4. Round | 01/09/2018 | Alloa Athletic | - | Dundee United | 1:1 | ||||
| 5. Round | 15/09/2018 | Dundee United | - | Greenock Morton FC | 1:1 | ||||
| 6. Round | 22/09/2018 | Falkirk FC | - | Dundee United | 0:2 | ||||
| 7. Round | 29/09/2018 | Dundee United | - | Ross County FC | 1:5 | ||||
| 15. Round | 30/11/2018 | Dundee United | - | Ayr United | 0:5 | ||||
| 16. Round | 08/12/2018 | Greenock Morton FC | - | Dundee United | 1:1 |
Slovakia