| 1. Round | 05/08/2023 | Elgin City | - | Stranraer FC | 0:1 |  |
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| 2. Round | 12/08/2023 | Stranraer FC | - | East Fife FC | 1:1 | ||||
| 3. Round | 19/08/2023 | Bonnyrigg Rose Athletic | - | Stranraer FC | 1:1 | ||||
| 4. Round | 26/08/2023 | Stranraer FC | - | Clyde FC | 1:0 | ||||
| 5. Round | 02/09/2023 | Stranraer FC | - | Peterhead FC | 2:1 | ||||
| 6. Round | 16/09/2023 | Stenhousemuir FC | - | Stranraer FC | 5:0 | ||||
| 7. Round | 23/09/2023 | Stranraer FC | - | Forfar Athletic | 0:2 | ||||
| 8. Round | 30/09/2023 | Dumbarton FC | - | Stranraer FC | 3:1 | |
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| 10. Round | 21/10/2023 | East Fife FC | - | Stranraer FC | 4:0 | ||||
| 11. Round | 04/11/2023 | Stranraer FC | - | Elgin City | 3:1 | |
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| 13. Round | 18/11/2023 | Stranraer FC | - | Stenhousemuir FC | 0:3 | ||||
| 14. Round | 02/12/2023 | Forfar Athletic | - | Stranraer FC | 1:1 | ||||
| 15. Round | 09/12/2023 | Clyde FC | - | Stranraer FC | 2:2 | |
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| 16. Round | 16/12/2023 | Stranraer FC | - | Bonnyrigg Rose Athletic | 3:1 |
Scotland