| 23. Round | 02/02/2019 | Falkirk FC | - | Queen Of The South | 3:0 | ||||
| 24. Round | 16/02/2019 | Queen Of The South | - | Dundee United | 0:1 | ||||
| 25. Round | 23/02/2019 | Queen Of The South | - | Alloa Athletic | 1:2 | ||||
| 27. Round | 02/03/2019 | Dunfermline Athletic | - | Queen Of The South | 1:0 | ||||
| 28. Round | 09/03/2019 | Queen Of The South | - | Inverness CT | 0:2 | ||||
| 31. Round | 30/03/2019 | Dundee United | - | Queen Of The South | 1:2 | ||||
| 30. Round | 02/04/2019 | Queen Of The South | - | Falkirk FC | 1:1 | ||||
| 32. Round | 06/04/2019 | Queen Of The South | - | Greenock Morton FC | 1:1 | ||||
| 29. Round | 09/04/2019 | Ayr United | - | Queen Of The South | 1:0 | ||||
| 33. Round | 13/04/2019 | Alloa Athletic | - | Queen Of The South | 1:0 | ||||
| 35. Round | 26/04/2019 | Ross County FC | - | Queen Of The South | 4:0 |
USA