| 5. Round | 02/09/2023 | Annagh United | - | Newington FC | 0:3 | ||||
| 6. Round | 09/09/2023 | Portadown FC | - | Annagh United | 4:1 |  |
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| 7. Round | 16/09/2023 | Ballyclare Comrades | - | Annagh United | 0:0 | ||||
| 9. Round | 30/09/2023 | Annagh United | - | H&W Welders | 2:1 | ||||
| 10. Round | 07/10/2023 | Bangor FC | - | Annagh United | 3:1 | ||||
| 11. Round | 13/10/2023 | Annagh United | - | Ballinamallard United FC | 0:0 | ||||
| 12. Round | 21/10/2023 | Ards FC | - | Annagh United | 2:3 | |
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| 13. Round | 28/10/2023 | Newington FC | - | Annagh United | 3:0 | ||||
| 14. Round | 04/11/2023 | Ballyclare Comrades | - | Annagh United | 2:2 | ||||
| 15. Round | 11/11/2023 | H&W Welders | - | Annagh United | 2:0 | ||||
| 17. Round | 25/11/2023 | Annagh United | - | Bangor FC | 0:4 | ||||
| 18. Round | 02/12/2023 | Ballinamallard United FC | - | Annagh United | 2:0 | ||||
| 8. Round | 05/12/2023 | Annagh United | - | Institute FC Drumahoe | 1:1 |  |
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| 19. Round | 09/12/2023 | Institute FC Drumahoe | - | Annagh United | 1:3 | ||||
| 20. Round | 16/12/2023 | Annagh United | - | Dergview FC | 3:0 | ||||
| 21. Round | 22/12/2023 | Dundela FC | - | Annagh United | 6:2 |
Northern Ireland