| 1. Round | 05/08/2023 | Maidenhead United | - | AFC Fylde | 2:2 | ||||
| 3. Round | 15/08/2023 | Hartlepool United | - | Maidenhead United | 3:1 | ||||
| 6. Round | 28/08/2023 | Kidderminster Harriers | - | Maidenhead United | 0:0 | ||||
| 11. Round | 23/09/2023 | Gateshead FC | - | Maidenhead United | 3:0 | ||||
| 12. Round | 26/09/2023 | Maidenhead United | - | Altrincham FC | 0:1 | ||||
| 13. Round | 30/09/2023 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
| 14. Round | 03/10/2023 | Oldham Athletic | - | Maidenhead United | 1:1 |  |
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| 15. Round | 07/10/2023 | Maidenhead United | - | Rochdale AFC | 2:2 | ||||
| 16. Round | 21/10/2023 | Barnet FC | - | Maidenhead United | 3:2 | |
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| 17. Round | 24/10/2023 | Aldershot Town | - | Maidenhead United | 4:2 | ||||
| 18. Round | 28/10/2023 | Maidenhead United | - | Eastleigh FC | 3:2 |  |
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| 23. Round | 02/12/2023 | Oxford City | - | Maidenhead United | 1:4 | ||||
| 25. Round | 23/12/2023 | Woking FC | - | Maidenhead United | 0:0 | ||||
| 26. Round | 26/12/2023 | Maidenhead United | - | Wealdstone FC | 0:2 | |
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| 29. Round | 13/02/2024 | Halifax Town | - | Maidenhead United | 2:1 |
England