| 18. Round | 08/11/2003 | Gillingham FC | - | Crewe Alexandra | 2:0 | ||||
| 19. Round | 15/11/2003 | Gillingham FC | - | Wimbledon FC | 1:2 | ||||
| 21. Round | 29/11/2003 | Gillingham FC | - | Stoke City | 3:1 | ||||
| 22. Round | 06/12/2003 | Crewe Alexandra | - | Gillingham FC | 1:1 | ||||
| 23. Round | 13/12/2003 | Gillingham FC | - | Preston North End | 0:1 | ||||
| 25. Round | 26/12/2003 | Gillingham FC | - | Watford FC | 1:0 |  |
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| 26. Round | 28/12/2003 | Millwall FC | - | Gillingham FC | 1:2 |  |
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| 27. Round | 10/01/2004 | Gillingham FC | - | Sheffield United | 0:3 | ||||
| 29. Round | 31/01/2004 | Gillingham FC | - | Bradford City | 1:0 | ||||
| 30. Round | 07/02/2004 | Burnley FC | - | Gillingham FC | 1:0 | ||||
| 32. Round | 21/02/2004 | Gillingham FC | - | Reading FC | 0:1 | ||||
| 24. Round | 25/02/2004 | Nottingham Forest | - | Gillingham FC | 0:0 | ||||
| 33. Round | 28/02/2004 | Crystal Palace | - | Gillingham FC | 1:0 | ||||
| 35. Round | 06/03/2004 | Gillingham FC | - | Nottingham Forest | 2:1 | |
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| 37. Round | 16/03/2004 | Norwich City | - | Gillingham FC | 3:0 | ||||
| 38. Round | 20/03/2004 | Gillingham FC | - | Rotherham United | 2:0 | ||||
| 31. Round | 23/03/2004 | Sunderland AFC | - | Gillingham FC | 2:1 |
England