| 5. Round | 13/09/2003 | Arsenal FC | - | Portsmouth FC | 1:1 | ||||
| 6. Round | 20/09/2003 | Portsmouth FC | - | Blackburn Rovers | 1:2 | ||||
| 7. Round | 27/09/2003 | Birmingham City | - | Portsmouth FC | 2:0 |  |
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| 8. Round | 04/10/2003 | Portsmouth FC | - | Charlton Athletic | 1:2 | |
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| 9. Round | 18/10/2003 | Portsmouth FC | - | Liverpool FC | 1:0 | ||||
| 10. Round | 25/10/2003 | Newcastle United | - | Portsmouth FC | 3:0 | ||||
| 11. Round | 01/11/2003 | Manchester United | - | Portsmouth FC | 3:0 | |
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| 12. Round | 08/11/2003 | Portsmouth FC | - | Leeds United | 6:1 | ||||
| 13. Round | 24/11/2003 | Fulham FC | - | Portsmouth FC | 2:0 | |
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| 14. Round | 29/11/2003 | Portsmouth FC | - | Leicester City | 0:2 | ||||
| 15. Round | 06/12/2003 | Middlesbrough FC | - | Portsmouth FC | 0:0 | ||||
| 17. Round | 21/12/2003 | Southampton FC | - | Portsmouth FC | 3:0 | |
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| 18. Round | 26/12/2003 | Portsmouth FC | - | Tottenham Hotspur | 2:0 | |
England
