| 6. Round | 28/08/2023 | Kidderminster Harriers | - | Maidenhead United | 0:0 | ||||
| 7. Round | 02/09/2023 | Maidenhead United | - | Woking FC | 0:0 | ||||
| 8. Round | 09/09/2023 | Bromley FC | - | Maidenhead United | 4:1 | ||||
| 9. Round | 16/09/2023 | Maidenhead United | - | Boreham Wood | 0:1 | ||||
| 10. Round | 19/09/2023 | Southend United | - | Maidenhead United | 2:0 | ||||
| 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 |  |
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| 14. Round | 03/10/2023 | Oldham Athletic | - | Maidenhead United | 1:1 | ||||
| 15. Round | 07/10/2023 | Maidenhead United | - | Rochdale AFC | 2:2 | ||||
| 16. Round | 21/10/2023 | Barnet FC | - | Maidenhead United | 3:2 | ||||
| 17. Round | 24/10/2023 | Aldershot Town | - | Maidenhead United | 4:2 | ||||
| 21. Round | 21/11/2023 | Ebbsfleet United | - | Maidenhead United | 1:1 |
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