| League Cup | 02.08.14 | Dunfermline Athletic | - | Annan Athletic | 5:1 |  |
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| League Two | 13.08.22 | Dumbarton FC | - | Annan Athletic | 4:0 | |
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| League Two | 29.10.22 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| League Two | 11.02.23 | Dumbarton FC | - | Annan Athletic | 2:1 | ||||
| League Two | 08.04.23 | Annan Athletic | - | Dumbarton FC | 3:1 |  |
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| Playoffs | 09.05.23 | Annan Athletic | - | Dumbarton FC | 6:0 | |
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| Playoffs | 13.05.23 | Dumbarton FC | - | Annan Athletic | 0:0 | ||||
| League One | 31.08.24 | Stenhousemuir FC | - | Annan Athletic | 5:1 | ||||
| League One | 09.11.24 | Annan Athletic | - | Stenhousemuir FC | 1:1 | ||||
| League One | 04.01.25 | Stenhousemuir FC | - | Annan Athletic | 1:1 | |
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| League One | 08.03.25 | Annan Athletic | - | Stenhousemuir FC | 0:2 | |
Schotland