League Two | 28/08/21 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
League Two | 30/10/21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
League Two | 09/04/22 | Annan Athletic | - | Cowdenbeath FC | 2:3 | ||||
League One | 12/08/23 | Annan Athletic | - | Montrose FC | 1:3 | ||||
League One | 11/11/23 | Montrose FC | - | Annan Athletic | 1:1 | ||||
League One | 06/01/24 | Annan Athletic | - | Montrose FC | 2:2 | ||||
League One | 16/03/24 | Montrose FC | - | Annan Athletic | 1:1 |