| League Two | 13.11.21 | Stenhousemuir FC | - | Annan Athletic | 2:0 | ||||
| League Two | 03.12.21 | Edinburgh City FC | - | Annan Athletic | 0:1 |  |
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| League Two | 02.01.22 | Stranraer FC | - | Annan Athletic | 1:1 | |
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| League Two | 23.12.22 | Annan Athletic | - | Albion Rovers | 5:1 | ||||
| League Two | 29.04.23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 0:0 | ||||
| League One | 28.11.23 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| League One | 27.01.24 | Annan Athletic | - | Edinburgh City | 3:0 | |
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| League One | 13.04.24 | Annan Athletic | - | Cove Rangers | 4:2 | |
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| League One | 24.08.24 | Annan Athletic | - | Alloa Athletic | 0:1 |
Inglaterra