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 |