Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 19.01.2019 |  | 4. Round | Raith Rovers - Dunfermline | Rai - DUN | 3:0 | 6.013 |
| 23.02.2019 |  | Matchday 26 | Raith Rovers - Montrose FC | Rai - Mon | 4:1 | 1.289 |
| 07.05.2019 |  | Semi-finals First leg | Raith Rovers - Forfar Athletic | Rai - FOR | 2:1 | 2.007 |
| 15.05.2019 | | Final First leg | Raith Rovers - Queen Of The South | Rai - | 1:3 | 2.471 |
| 13.07.2019 |  | Group D | Raith Rovers - Dundee FC | Rai - Dun | 0:3 | 2.584 |
| 23.07.2019 | | Group D | Raith Rovers - Peterhead | Rai - Pet | 3:1 | 788 |