League Cup | 15/07/17 | Clyde FC | - | Annan Athletic | 2:1 | ||||
League Two | 14/08/21 | Annan Athletic | - | Stirling Albion FC | 3:1 | ||||
League Two | 19/03/22 | Stirling Albion FC | - | Annan Athletic | 0:3 | ||||
League Two | 13/08/22 | Dumbarton FC | - | Annan Athletic | 4:0 | ||||
League Two | 29/10/22 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
League Two | 11/02/23 | Dumbarton FC | - | Annan Athletic | 2:1 | ||||
League Two | 08/04/23 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
Playoffs | 09/05/23 | Annan Athletic | - | Dumbarton FC | 6:0 | ||||
Playoffs | 13/05/23 | Dumbarton FC | - | Annan Athletic | 0:0 |