| League Two | 11.09.21 | Annan Athletic | - | Stenhousemuir FC | 1:2 |  |
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| League Two | 05.02.22 | Annan Athletic | - | Stenhousemuir FC | 0:2 | |
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| League Two | 02.04.22 | Stenhousemuir FC | - | Annan Athletic | 0:1 | |
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| League Two | 06.08.22 | Annan Athletic | - | Stenhousemuir FC | 2:1 | ||||
| League Two | 08.10.22 | Stenhousemuir FC | - | Annan Athletic | 2:2 | ||||
| League Two | 04.03.23 | Annan Athletic | - | Stenhousemuir FC | 2:3 | ||||
| League Two | 06.05.23 | Stenhousemuir FC | - | Annan Athletic | 2:1 | ||||
| League One | 02.09.23 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| League One | 04.11.23 | Annan Athletic | - | Kelty Hearts | 2:2 | ||||
| League One | 13.01.24 | Kelty Hearts | - | Annan Athletic | 1:1 |
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