League Two | 16/10/21 | Forfar Athletic | - | Annan Athletic | 2:0 | ||||
League Cup | 16/07/22 | Annan Athletic | - | Elgin City | 4:0 | ||||
League Two | 20/08/22 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
Playoffs | 13/05/23 | Dumbarton FC | - | Annan Athletic | 0:0 | ||||
League Cup | 22/07/23 | Annan Athletic | - | Albion Rovers | 1:2 |