| League Two | 07.08.21 | Stranraer FC | - | Annan Athletic | 0:3 |  |
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| League Two | 06.11.21 | Annan Athletic | - | Stranraer FC | 2:2 | ||||
| League Two | 02.01.22 | Stranraer FC | - | Annan Athletic | 1:1 | ||||
| League Two | 05.03.22 | Annan Athletic | - | Stranraer FC | 4:1 | ||||
| League Two | 06.08.22 | Annan Athletic | - | Stenhousemuir FC | 2:1 |  |
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| League Two | 08.10.22 | Stenhousemuir FC | - | Annan Athletic | 2:2 | ||||
| League Two | 04.03.23 | Annan Athletic | - | Stenhousemuir FC | 2:3 | |
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| 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 | |
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| League One | 04.01.25 | Stenhousemuir FC | - | Annan Athletic | 1:1 | ||||
| League One | 08.03.25 | Annan Athletic | - | Stenhousemuir FC | 0:2 | |
Schottland