| 2. Round | 16/08/2003 | Cambridge United | - | Macclesfield Town | 3:1 | ||||
| 8. Round | 16/09/2003 | Swansea City | - | Macclesfield Town | 3:0 | ||||
| 9. Round | 20/09/2003 | Northampton Town | - | Macclesfield Town | 0:0 | ||||
| 10. Round | 27/09/2003 | Macclesfield Town | - | York City | 0:0 | ||||
| 11. Round | 30/09/2003 | Macclesfield Town | - | Rochdale AFC | 2:1 | ||||
| 12. Round | 04/10/2003 | Leyton Orient | - | Macclesfield Town | 2:0 |  |
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| 13. Round | 11/10/2003 | Macclesfield Town | - | Doncaster Rovers | 1:3 | |
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| 14. Round | 18/10/2003 | Carlisle United | - | Macclesfield Town | 0:1 | |
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| 19. Round | 22/11/2003 | Oxford United | - | Macclesfield Town | 3:1 |
England