League Two | 21/08/21 | Albion Rovers | - | Annan Athletic | 0:1 | ||||
League Two | 30/10/21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
FA Cup | 27/11/21 | Gala Fairydean Rovers | - | Annan Athletic | 0:1 | ||||
League Two | 03/09/22 | Annan Athletic | - | Forfar Athletic | 2:1 | ||||
League One | 02/09/23 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
League Two | 05/03/24 | Stranraer FC | - | Dumbarton FC | 5:0 | ||||
League Two | 23/03/24 | East Fife FC | - | Stranraer FC | 2:1 |