| Playoffs | 07.05.19 | Annan Athletic | - | Stenhousemuir FC | 2:0 |  |
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| League Two | 28.08.21 | Stenhousemuir FC | - | Kelty Hearts | 1:4 | ||||
| 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 | 09.11.24 | Annan Athletic | - | Stenhousemuir FC | 1:1 |
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