| 2. Round | 16/08/2003 | Cambridge United | - | Macclesfield Town | 3:1 | ||||
| 3. Round | 23/08/2003 | Macclesfield Town | - | Torquay United | 1:1 |  |
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| 4. Round | 25/08/2003 | Bristol Rovers | - | Macclesfield Town | 2:2 | ||||
| 5. Round | 30/08/2003 | Macclesfield Town | - | Yeovil Town | 4:1 | ||||
| 6. Round | 06/09/2003 | Mansfield Town | - | Macclesfield Town | 3:2 | |
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| 7. Round | 13/09/2003 | Macclesfield Town | - | Kidderminster Harriers | 1:1 | ||||
| 8. Round | 16/09/2003 | Swansea City | - | Macclesfield Town | 3:0 | ||||
| 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 | ||||
| 13. Round | 11/10/2003 | Macclesfield Town | - | Doncaster Rovers | 1:3 | ||||
| 14. Round | 18/10/2003 | Carlisle United | - | Macclesfield Town | 0:1 | ||||
| 15. Round | 21/10/2003 | Lincoln City | - | Macclesfield Town | 3:2 | ||||
| 16. Round | 25/10/2003 | Macclesfield Town | - | Southend United | 1:2 | ||||
| 19. Round | 22/11/2003 | Oxford United | - | Macclesfield Town | 3:1 |
England
