| League Two | 18/12/21 | Stirling Albion FC | - | Annan Athletic | 2:3 |  |
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| League Two | 29/01/22 | Annan Athletic | - | Stirling Albion FC | 0:0 | ||||
| League Two | 19/03/22 | Stirling Albion FC | - | Annan Athletic | 0:3 | ||||
| League Two | 20/08/22 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
| League Two | 12/11/22 | Stirling Albion FC | - | Annan Athletic | 0:2 | ||||
| League Two | 18/02/23 | Annan Athletic | - | Stirling Albion FC | 2:2 | ||||
| League Two | 22/04/23 | Stirling Albion FC | - | Annan Athletic | 3:1 | ||||
| League One | 16/09/23 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| League One | 16/12/23 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| League One | 17/02/24 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| League One | 04/05/24 | Stirling Albion FC | - | Annan Athletic | 1:1 | |
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| League One | 31/08/24 | Stenhousemuir FC | - | Annan Athletic | 5:1 |
Scotland