| 3. Round | 23/08/2003 | Bradford City | - | Gillingham FC | 0:1 | ||||
| 4. Round | 25/08/2003 | Gillingham FC | - | Burnley FC | 0:3 | ||||
| 5. Round | 30/08/2003 | Watford FC | - | Gillingham FC | 2:2 | ||||
| 6. Round | 06/09/2003 | Gillingham FC | - | Millwall FC | 4:3 |  |
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| 7. Round | 13/09/2003 | Cardiff City | - | Gillingham FC | 5:0 | ||||
| 8. Round | 16/09/2003 | Gillingham FC | - | Norwich City | 1:2 | |
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| 9. Round | 20/09/2003 | Gillingham FC | - | West Ham United | 2:0 | |
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| 10. Round | 27/09/2003 | Rotherham United | - | Gillingham FC | 1:1 | ||||
| 12. Round | 04/10/2003 | Gillingham FC | - | West Bromwich Albion | 0:2 | ||||
| 14. Round | 14/10/2003 | Reading FC | - | Gillingham FC | 2:1 | |
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| 15. Round | 18/10/2003 | Wigan Athletic | - | Gillingham FC | 1:0 |
England