1. Round | 04/08/2018 | Dundee United | - | Dunfermline Athletic | 2:3 | ||||
2. Round | 11/08/2018 | Queen Of The South | - | Dundee United | 1:2 | ||||
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 | ||||
8. Round | 06/10/2018 | Ayr United | - | Dundee United | 2:0 | ||||
10. Round | 27/10/2018 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
13. Round | 10/11/2018 | Ross County FC | - | Dundee United | 0:1 | ||||
14. Round | 20/11/2018 | Dundee United | - | Alloa Athletic | 4:2 | ||||
16. Round | 08/12/2018 | Greenock Morton FC | - | Dundee United | 1:1 | ||||
17. Round | 15/12/2018 | Inverness CT | - | Dundee United | 1:1 |