| 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 | |
|||
| Playoffs | 03/05/22 | Annan Athletic | - | Forfar Athletic | 1:0 |
England