| League Two | 31.07.21 | Annan Athletic | - | Forfar Athletic | 0:2 |  |
|||
| League Two | 16.10.21 | Forfar Athletic | - | Annan Athletic | 2:0 | ||||
| League Two | 15.01.22 | Annan Athletic | - | Forfar Athletic | 2:2 | ||||
| League Two | 16.04.22 | Forfar Athletic | - | Annan Athletic | 5:1 | ||||
| Playoffs | 03.05.22 | Annan Athletic | - | Forfar Athletic | 1:0 | ||||
| Playoffs | 07.05.22 | Forfar Athletic | - | Annan Athletic | 1:1 | ||||
| League Two | 17.09.22 | Annan Athletic | - | East Fife FC | 2:2 | |
|||
| League Two | 03.12.22 | East Fife FC | - | Annan Athletic | 1:3 | ||||
| League Two | 28.01.23 | Annan Athletic | - | East Fife FC | 3:0 | ||||
| League Two | 01.04.23 | East Fife FC | - | Annan Athletic | 0:1 |
Écosse