| 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 |
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