| 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 |  |
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| Playoffs | 03/05/22 | Annan Athletic | - | Forfar Athletic | 1:0 |  |
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| Playoffs | 07/05/22 | Forfar Athletic | - | Annan Athletic | 1:1 | ||||
| League Two | 03/09/22 | Annan Athletic | - | Forfar Athletic | 2:1 | |
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| League Two | 05/11/22 | Forfar Athletic | - | Annan Athletic | 1:4 | |
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| League Two | 18/03/23 | Forfar Athletic | - | Annan Athletic | 2:1 | |
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| League One | 31/08/24 | Stenhousemuir FC | - | Annan Athletic | 5:1 | ||||
| League One | 09/11/24 | Annan Athletic | - | Stenhousemuir FC | 1:1 | |
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| League One | 08/03/25 | Annan Athletic | - | Stenhousemuir FC | 0:2 |
Scotland