| 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 |
Scotland