League Two | 28/08/21 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
League Two | 30/10/21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
League Two | 08/01/22 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
League Two | 09/04/22 | Annan Athletic | - | Cowdenbeath FC | 2:3 | ||||
League One | 23/09/23 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
League One | 03/02/24 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
League One | 30/03/24 | Alloa Athletic | - | Annan Athletic | 1:1 |