| 2. Round | 12/08/2023 | Ballinamallard United FC | - | Dergview FC | 4:2 | ||||
| 3. Round | 19/08/2023 | H&W Welders | - | Dergview FC | 2:3 | ||||
| 4. Round | 26/08/2023 | Dergview FC | - | Annagh United | 0:1 | ||||
| 5. Round | 02/09/2023 | Dergview FC | - | Dundela FC | 0:1 | ||||
| 6. Round | 09/09/2023 | Newington FC | - | Dergview FC | 3:2 |  |
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| 8. Round | 23/09/2023 | Dergview FC | - | Knockbreda FC | 5:0 | |
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| 9. Round | 30/09/2023 | Dergview FC | - | Bangor FC | 2:1 | ||||
| 10. Round | 07/10/2023 | Institute FC Drumahoe | - | Dergview FC | 2:0 | ||||
| 11. Round | 13/10/2023 | Ballyclare Comrades | - | Dergview FC | 2:2 | ||||
| 12. Round | 21/10/2023 | Dergview FC | - | Newington FC | 2:1 | ||||
| 14. Round | 04/11/2023 | Dergview FC | - | Ards FC | 0:3 | ||||
| 15. Round | 11/11/2023 | Portadown FC | - | Dergview FC | 4:1 | ||||
| 17. Round | 25/11/2023 | Knockbreda FC | - | Dergview FC | 2:0 | ||||
| 18. Round | 01/12/2023 | Dergview FC | - | Institute FC Drumahoe | 2:2 | ||||
| 13. Round | 05/12/2023 | Dundela FC | - | Dergview FC | 3:2 | ||||
| 20. Round | 16/12/2023 | Annagh United | - | Dergview FC | 3:0 |
Northern Ireland