| League Cup | 29/07/17 | Elgin City | - | Peterhead FC | 0:3 | ||||
| Playoffs | 10/05/22 | Edinburgh City FC | - | Annan Athletic | 2:0 | ||||
| Playoffs | 19/05/23 | Clyde FC | - | Annan Athletic | 1:2 | ||||
| League One | 26/08/23 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
| League One | 09/03/24 | Annan Athletic | - | Queen Of The South | 2:1 | ||||
| League One | 05/04/25 | Annan Athletic | - | Queen Of The South | 0:2 | ||||
| Playoffs | 16/05/25 | Annan Athletic | - | East Fife FC | 1:1 |
Scotland