| 1. Round | 05/08/2023 | Annagh United | - | Dundela FC | 5:2 |  |
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| 2. Round | 12/08/2023 | Knockbreda FC | - | Annagh United | 0:1 | |
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| 3. Round | 19/08/2023 | Annagh United | - | Ards FC | 0:0 | ||||
| 4. Round | 26/08/2023 | Dergview FC | - | Annagh United | 0:1 | ||||
| 5. Round | 02/09/2023 | Annagh United | - | Newington FC | 0:3 | ||||
| 22. Round | 26/12/2023 | Annagh United | - | Portadown FC | 3:1 | ||||
| 23. Round | 30/12/2023 | Bangor FC | - | Annagh United | 2:1 | ||||
| 24. Round | 13/01/2024 | Annagh United | - | Institute FC Drumahoe | 0:0 | |
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| 25. Round | 19/01/2024 | Annagh United | - | Ards FC | 2:0 | ||||
| 26. Round | 27/01/2024 | Knockbreda FC | - | Annagh United | 1:4 |  |
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| 27. Round | 10/02/2024 | Annagh United | - | Portadown FC | 2:2 | |
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| 29. Round | 23/02/2024 | Annagh United | - | Dundela FC | 4:0 | ||||
| 30. Round | 02/03/2024 | Annagh United | - | H&W Welders | 4:3 | ||||
| 31. Round | 09/03/2024 | Annagh United | - | Ballyclare Comrades | 2:1 | ||||
| 32. Round | 16/03/2024 | Annagh United | - | Newington FC | 2:0 | |
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| 33. Round | 23/03/2024 | Ballinamallard United FC | - | Annagh United | 1:0 |
Northern Ireland