| 4. Round | 25/08/2003 | Chesterfield FC | - | Plymouth Argyle | 1:1 | ||||
| 5. Round | 30/08/2003 | Queens Park Rangers | - | Chesterfield FC | 3:0 | ||||
| 6. Round | 06/09/2003 | Chesterfield FC | - | Barnsley FC | 0:2 | ||||
| 7. Round | 13/09/2003 | Chesterfield FC | - | Notts County | 0:1 |  |
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| 8. Round | 16/09/2003 | Brighton & Hove Albion | - | Chesterfield FC | 1:0 | ||||
| 9. Round | 20/09/2003 | Grimsby Town | - | Chesterfield FC | 4:0 | ||||
| 42. Round | 12/04/2004 | AFC Bournemouth | - | Chesterfield FC | 2:2 | |
England
Ireland