1. Round | 04/08/2018 | Dundee United | - | Dunfermline Athletic | 2:3 | ||||
2. Round | 11/08/2018 | Queen Of The South | - | Dundee United | 1:2 | ||||
8. Round | 06/10/2018 | Ayr United | - | Dundee United | 2:0 | ||||
17. Round | 15/12/2018 | Inverness CT | - | Dundee United | 1:1 | ||||
18. Round | 22/12/2018 | Dundee United | - | Falkirk FC | 2:1 | ||||
20. Round | 05/01/2019 | Dundee United | - | Partick Thistle | 1:1 | ||||
21. Round | 12/01/2019 | Dundee United | - | Dunfermline Athletic | 1:0 | ||||
32. Round | 05/04/2019 | Ross County FC | - | Dundee United | 1:1 |