| 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 | ||||
| League Two | 06.05.23 | Stenhousemuir FC | - | Annan Athletic | 2:1 | ||||
| League One | 14.12.24 | Queen Of The South | - | Stenhousemuir FC | 2:1 | ||||
| League One | 08.02.25 | Stenhousemuir FC | - | Queen Of The South | 2:1 |
Guadalupe