| League Two | 31/07/21 | Annan Athletic | - | Forfar Athletic | 0:2 |  |
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| 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 | |
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| 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 | ||||
| Playoffs | 13/05/25 | East Fife FC | - | Annan Athletic | 3:2 | ||||
| Playoffs | 16/05/25 | Annan Athletic | - | East Fife FC | 1:1 |
Scotland