| 20. Round | 29/11/2003 | Torquay United | - | Southend United | 3:0 | ||||
| 27. Round | 17/01/2004 | Southend United | - | Doncaster Rovers | 0:2 | ||||
| 28. Round | 24/01/2004 | Mansfield Town | - | Southend United | 1:0 | ||||
| 25. Round | 27/01/2004 | Southend United | - | York City | 0:0 | ||||
| 30. Round | 07/02/2004 | Southend United | - | Cambridge United | 1:0 | ||||
| 44. Round | 24/04/2004 | Southend United | - | Yeovil Town | 0:2 |
England