| League Cup | 21.07.18 | Livingston FC | - | Annan Athletic | 1:0 | ||||
| League Two | 22.04.22 | Edinburgh City FC | - | Annan Athletic | 2:1 | ||||
| Playoffs | 10.05.22 | Edinburgh City FC | - | Annan Athletic | 2:0 | ||||
| Playoffs | 13.05.22 | Annan Athletic | - | Edinburgh City FC | 2:1 | ||||
| League One | 26.08.23 | Annan Athletic | - | Edinburgh City | 3:2 |  |
|||
| League One | 28.10.23 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| League One | 17.02.24 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| League One | 04.05.24 | Stirling Albion FC | - | Annan Athletic | 1:1 |
Schottland