| League Two | 07/08/21 | Stranraer FC | - | Annan Athletic | 0:3 | ||||
| League Two | 25/09/21 | Annan Athletic | - | Edinburgh City FC | 1:3 |  |
|||
| League Two | 20/11/21 | Annan Athletic | - | Albion Rovers | 1:1 | ||||
| League Two | 08/01/22 | Cowdenbeath FC | - | Annan Athletic | 1:3 | |
|||
| League Two | 22/04/22 | Edinburgh City FC | - | Annan Athletic | 2:1 | ||||
| Playoffs | 03/05/22 | Annan Athletic | - | Forfar Athletic | 1:0 | ||||
| League Cup | 19/07/22 | Annan Athletic | - | Ayr United | 5:4 pso | ||||
| League Two | 21/01/23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| League Two | 15/04/23 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| League Cup | 18/07/23 | Dunfermline Athletic | - | Annan Athletic | 4:0 | ||||
| League One | 30/03/24 | Alloa Athletic | - | Annan Athletic | 1:1 |
England