Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 07.05.2019 |  | Semi-finals First leg | Annan Athletic - Stenhousemuir | - Ste | 2:0 | 637 |
| 14.05.2019 | | Final First leg | Annan Athletic - Clyde FC | - | 1:0 | 1.006 |
| 23.07.2019 |  | Group E | Annan Athletic - Morton | - Mor | 0:5 | 478 |
Galabank