| 10. Round | 19/09/2023 | Southend United | - | Maidenhead United | 2:0 | ||||
| 11. Round | 23/09/2023 | Southend United | - | AFC Fylde | 1:2 | ||||
| 13. Round | 30/09/2023 | Rochdale AFC | - | Southend United | 2:2 | ||||
| 14. Round | 03/10/2023 | Southend United | - | Oxford City | 2:0 | ||||
| 15. Round | 07/10/2023 | Woking FC | - | Southend United | 0:2 | ||||
| 16. Round | 21/10/2023 | Southend United | - | Solihull Moors | 5:0 | ||||
| 17. Round | 24/10/2023 | Southend United | - | Ebbsfleet United | 3:0 | ||||
| 18. Round | 28/10/2023 | Boreham Wood | - | Southend United | 1:1 | ||||
| 22. Round | 25/11/2023 | Gateshead FC | - | Southend United | 1:1 | ||||
| 24. Round | 16/12/2023 | Southend United | - | Bromley FC | 1:2 | ||||
| 25. Round | 23/12/2023 | Kidderminster Harriers | - | Southend United | 1:2 | ||||
| 26. Round | 26/12/2023 | Southend United | - | Barnet FC | 0:2 | ||||
| 27. Round | 30/12/2023 | Barnet FC | - | Southend United | 1:0 |  |
Portugal
São Tomé and Príncipe