2. Round | 12/08/2023 | Dorking Wanderers | - | Maidenhead United | 0:2 | ||||
3. Round | 15/08/2023 | Hartlepool United | - | Maidenhead United | 3:1 | ||||
4. Round | 19/08/2023 | Maidenhead United | - | Dagenham & Redbridge | 1:0 | ||||
5. Round | 26/08/2023 | Maidenhead United | - | Oxford City | 0:0 | ||||
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 | ||||
12. Round | 26/09/2023 | Maidenhead United | - | Altrincham FC | 0:1 | ||||
14. Round | 03/10/2023 | Oldham Athletic | - | Maidenhead United | 1:1 | ||||
15. Round | 07/10/2023 | Maidenhead United | - | Rochdale AFC | 2:2 |