Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 29.01.2019 |  | 4. Round Repeat | Stenhousemuir - Aberdeen | Ste - ABE | 1:4 | 2.429 |
| 11.05.2019 |  | Semi-finals 2nd leg | Stenhousemuir - Annan Athletic | Ste - | 1:2 | 794 |
| 16.07.2019 |  | Group A | Stenhousemuir - Dundee Utd | Ste - DUN | 1:2 | 1.156 |
| 17.07.2019 | | Group F | Clyde FC - Hamilton | - Ham | 1:3 | 504 |
| 27.07.2019 | | Group A | Stenhousemuir - Cowdenbeath FC | Ste - | 2:0 | 262 |