| League Two | 07.08.21 | Stranraer FC | - | Annan Athletic | 0:3 |  |
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| League Two | 25.09.21 | Annan Athletic | - | Edinburgh City FC | 1:3 |  |
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| League Two | 20.11.21 | Annan Athletic | - | Albion Rovers | 1:1 | ||||
| League Two | 08.01.22 | Cowdenbeath FC | - | Annan Athletic | 1:3 | |
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| Playoffs | 03.05.22 | Annan Athletic | - | Forfar Athletic | 1:0 |
Angleterre