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 | ||||
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 | ||||
12. Round | 26/09/2023 | Aldershot Town | - | Southend United | 1:1 | ||||
45. Round | 13/04/2024 | AFC Fylde | - | Southend United | 0:2 | ||||
46. Round | 20/04/2024 | Southend United | - | Rochdale AFC | 1:2 |