| 10. Round | 27/09/2003 | Scunthorpe United | - | Southend United | 1:1 |  |
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| 11. Round | 30/09/2003 | Darlington FC | - | Southend United | 0:0 | ||||
| 12. Round | 04/10/2003 | Southend United | - | Huddersfield Town | 1:2 | ||||
| 13. Round | 11/10/2003 | Kidderminster Harriers | - | Southend United | 1:2 | |
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| 14. Round | 18/10/2003 | Southend United | - | Leyton Orient | 1:2 | |
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| 15. Round | 21/10/2003 | Southend United | - | Boston United | 0:2 | ||||
| 24. Round | 28/12/2003 | Southend United | - | Oxford United | 0:1 |
Scotland