| 1. Round | 09/08/2003 | Southend United | - | Cheltenham Town | 2:0 | ||||
| 2. Round | 16/08/2003 | Doncaster Rovers | - | Southend United | 2:0 | ||||
| 3. Round | 23/08/2003 | Southend United | - | Mansfield Town | 0:3 | ||||
| 15. Round | 21/10/2003 | Southend United | - | Boston United | 0:2 | ||||
| 17. Round | 01/11/2003 | Southend United | - | Northampton Town | 0:1 | ||||
| 18. Round | 15/11/2003 | Yeovil Town | - | Southend United | 4:0 | ||||
| 20. Round | 29/11/2003 | Torquay United | - | Southend United | 3:0 | ||||
| 22. Round | 20/12/2003 | Southend United | - | Bristol Rovers | 0:1 | ||||
| 45. Round | 01/05/2004 | Rochdale AFC | - | Southend United | 1:1 |
England
St. Lucia