Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 09.01.2016 |  | 4. Round | Annan Athletic - Hamilton | - Ham | 4:1 | 817 |
| 06.02.2016 | | Round of 16 | Annan Athletic - Morton | - Mor | 1:4 | 756 |
| 16.07.2016 |  | Group F | Annan Athletic - Stranraer FC | - Str | 1:2 | 418 |
| 23.07.2016 | | Group F | Annan Athletic - Motherwell | - MOT | 1:3 | 956 |