1. Round | 05/08/2023 | Southend United | - | Oldham Athletic | 4:0 | ||||
2. Round | 12/08/2023 | Dagenham & Redbridge | - | Southend United | 0:2 | ||||
3. Round | 15/08/2023 | Dorking Wanderers | - | Southend United | 2:1 | ||||
4. Round | 19/08/2023 | Southend United | - | Hartlepool United | 2:3 | ||||
5. Round | 25/08/2023 | Southend United | - | Eastleigh FC | 2:0 | ||||
6. Round | 28/08/2023 | Bromley FC | - | Southend United | 2:1 | ||||
7. Round | 02/09/2023 | Southend United | - | Kidderminster Harriers | 2:1 | ||||
8. Round | 09/09/2023 | Halifax Town | - | Southend United | 1:1 | ||||
9. Round | 16/09/2023 | York City | - | Southend United | 3:0 | ||||
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 | ||||
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 |