| 1. Round | 09/08/2003 | Macclesfield Town | - | Boston United | 0:0 | ||||
| 2. Round | 16/08/2003 | Cambridge United | - | Macclesfield Town | 3:1 | ||||
| 11. Round | 30/09/2003 | Macclesfield Town | - | Rochdale AFC | 2:1 | ||||
| 15. Round | 21/10/2003 | Lincoln City | - | Macclesfield Town | 3:2 | ||||
| 16. Round | 25/10/2003 | Macclesfield Town | - | Southend United | 1:2 | ||||
| 18. Round | 15/11/2003 | Macclesfield Town | - | Scunthorpe United | 2:2 | ||||
| 19. Round | 22/11/2003 | Oxford United | - | Macclesfield Town | 3:1 | ||||
| 23. Round | 26/12/2003 | Cheltenham Town | - | Macclesfield Town | 3:2 |  |
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| 26. Round | 10/01/2004 | Boston United | - | Macclesfield Town | 3:1 | ||||
| 27. Round | 17/01/2004 | Macclesfield Town | - | Cambridge United | 0:1 |
England