| 4. Round | 21/08/2021 | Stenhousemuir FC | - | Cowdenbeath FC | 1:1 |  |
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| 8. Round | 25/09/2021 | Stenhousemuir FC | - | Elgin City | 1:2 | ||||
| 9. Round | 02/10/2021 | Stenhousemuir FC | - | Forfar Athletic | 1:1 | ||||
| 10. Round | 16/10/2021 | Cowdenbeath FC | - | Stenhousemuir FC | 0:2 | ||||
| 11. Round | 09/11/2021 | Stenhousemuir FC | - | Albion Rovers | 3:1 | ||||
| 13. Round | 13/11/2021 | Stenhousemuir FC | - | Annan Athletic | 2:0 | ||||
| 14. Round | 20/11/2021 | Kelty Hearts | - | Stenhousemuir FC | 2:0 |
Scotland