| FA Cup | 29/11/14 | Annan Athletic | - | Brechin City FC | 1:1 | ||||
| FA Cup | 09/12/14 | Brechin City FC | - | Annan Athletic | 4:2 | ||||
| League Two | 11/09/21 | Annan Athletic | - | Stenhousemuir FC | 1:2 | ||||
| League Two | 05/02/22 | Annan Athletic | - | Stenhousemuir FC | 0:2 | ||||
| League Two | 02/04/22 | Stenhousemuir FC | - | Annan Athletic | 0:1 | ||||
| League Two | 20/08/22 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
| League Two | 18/02/23 | Annan Athletic | - | Stirling Albion FC | 2:2 | ||||
| League One | 16/09/23 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| League One | 16/12/23 | Stirling Albion FC | - | Annan Athletic | 1:1 |
Scotland