10. Round | 19/09/2023 | Southend United | - | Maidenhead United | 2:0 | ||||
11. Round | 23/09/2023 | Southend United | - | AFC Fylde | 1:2 | ||||
12. Round | 26/09/2023 | Aldershot Town | - | Southend United | 1:1 | ||||
13. Round | 30/09/2023 | Rochdale AFC | - | Southend United | 2:2 | ||||
14. Round | 03/10/2023 | Southend United | - | Oxford City | 2:0 | ||||
19. Round | 11/11/2023 | Altrincham FC | - | Southend United | 2:0 | ||||
20. Round | 18/11/2023 | Southend United | - | Chesterfield FC | 2:1 | ||||
22. Round | 25/11/2023 | Gateshead FC | - | Southend United | 1:1 | ||||
24. Round | 16/12/2023 | Southend United | - | Bromley FC | 1:2 |