21. Round | 12/01/2019 | Dundee United | - | Dunfermline Athletic | 1:0 | ||||
22. Round | 25/01/2019 | Ayr United | - | Dundee United | 1:0 | ||||
23. Round | 02/02/2019 | Dundee United | - | Greenock Morton FC | 2:1 | ||||
25. Round | 23/02/2019 | Falkirk FC | - | Dundee United | 1:1 | ||||
28. Round | 09/03/2019 | Partick Thistle | - | Dundee United | 2:1 | ||||
27. Round | 19/03/2019 | Dundee United | - | Ross County FC | 1:0 | ||||
30. Round | 23/03/2019 | Dundee United | - | Alloa Athletic | 2:1 | ||||
36. Round | 04/05/2019 | Greenock Morton FC | - | Dundee United | 1:0 |