| League Two | 13/11/21 | Stenhousemuir FC | - | Annan Athletic | 2:0 |  |
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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 | ||||
| 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 | |
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| 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 | |
Scotland