| 2. Round | 06/08/2022 | Annan Athletic | - | Stenhousemuir FC | 2:1 | ||||
| 3. Round | 13/08/2022 | Stirling Albion FC | - | Stenhousemuir FC | 3:0 |  |
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| 5. Round | 27/08/2022 | Forfar Athletic | - | Stenhousemuir FC | 1:2 | ||||
| 6. Round | 03/09/2022 | Stenhousemuir FC | - | Stranraer FC | 3:1 | ||||
| 8. Round | 17/09/2022 | Stenhousemuir FC | - | Elgin City | 3:3 | ||||
| 7. Round | 20/09/2022 | East Fife FC | - | Stenhousemuir FC | 1:2 | ||||
| 11. Round | 15/10/2022 | Stenhousemuir FC | - | Stirling Albion FC | 1:3 | ||||
| 12. Round | 29/10/2022 | Albion Rovers | - | Stenhousemuir FC | 2:2 | ||||
| 13. Round | 05/11/2022 | Stenhousemuir FC | - | East Fife FC | 2:2 | |
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| 16. Round | 03/12/2022 | Elgin City | - | Stenhousemuir FC | 2:1 |  |
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| 20. Round | 07/01/2023 | Stenhousemuir FC | - | Stranraer FC | 2:1 | ||||
| 21. Round | 14/01/2023 | East Fife FC | - | Stenhousemuir FC | 1:1 | ||||
| 22. Round | 28/01/2023 | Stenhousemuir FC | - | Elgin City | 2:0 | ||||
| 31. Round | 01/04/2023 | Dumbarton FC | - | Stenhousemuir FC | 1:2 | ||||
| 32. Round | 08/04/2023 | Stenhousemuir FC | - | Bonnyrigg Rose Athletic | 0:0 | ||||
| 33. Round | 15/04/2023 | Stenhousemuir FC | - | Stirling Albion FC | 0:1 |
Scotland