| 1. Round | 05/08/2023 | Elgin City | - | Stranraer FC | 0:1 | ||||
| 2. Round | 12/08/2023 | Forfar Athletic | - | Elgin City | 0:0 | ||||
| 3. Round | 19/08/2023 | The Spartans FC | - | Elgin City | 2:1 | ||||
| 4. Round | 26/08/2023 | Elgin City | - | East Fife FC | 1:1 | ||||
| 5. Round | 02/09/2023 | Bonnyrigg Rose Athletic | - | Elgin City | 5:1 | ||||
| 8. Round | 30/09/2023 | Peterhead FC | - | Elgin City | 6:0 | ||||
| 9. Round | 24/10/2023 | Elgin City | - | Stenhousemuir FC | 1:1 | ||||
| 11. Round | 04/11/2023 | Stranraer FC | - | Elgin City | 3:1 | ||||
| 12. Round | 11/11/2023 | Elgin City | - | Bonnyrigg Rose Athletic | 2:0 | ||||
| 13. Round | 18/11/2023 | Dumbarton FC | - | Elgin City | 1:0 | ||||
| 10. Round | 21/11/2023 | Elgin City | - | Forfar Athletic | 1:0 | ||||
| 15. Round | 09/12/2023 | East Fife FC | - | Elgin City | 4:0 | ||||
| 16. Round | 16/12/2023 | Elgin City | - | The Spartans FC | 0:4 | ||||
| 17. Round | 23/12/2023 | Stenhousemuir FC | - | Elgin City | 2:0 | ||||
| 18. Round | 30/12/2023 | Elgin City | - | Peterhead FC | 2:1 | ||||
| 20. Round | 13/01/2024 | Forfar Athletic | - | Elgin City | 2:1 |
Scotland