| 2. Round | 16/08/2003 | Cambridge United | - | Macclesfield Town | 3:1 | ||||
| 3. Round | 23/08/2003 | Macclesfield Town | - | Torquay United | 1:1 | ||||
| 4. Round | 25/08/2003 | Bristol Rovers | - | Macclesfield Town | 2:2 | ||||
| 5. Round | 30/08/2003 | Macclesfield Town | - | Yeovil Town | 4:1 | ||||
| 7. Round | 13/09/2003 | Macclesfield Town | - | Kidderminster Harriers | 1:1 | ||||
| 8. Round | 16/09/2003 | Swansea City | - | Macclesfield Town | 3:0 |  |
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| 9. Round | 20/09/2003 | Northampton Town | - | Macclesfield Town | 0:0 | ||||
| 10. Round | 27/09/2003 | Macclesfield Town | - | York City | 0:0 | ||||
| 13. Round | 11/10/2003 | Macclesfield Town | - | Doncaster Rovers | 1:3 |  |
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| 26. Round | 10/01/2004 | Boston United | - | Macclesfield Town | 3:1 | ||||
| 29. Round | 31/01/2004 | Yeovil Town | - | Macclesfield Town | 2:2 | ||||
| 30. Round | 07/02/2004 | Macclesfield Town | - | Cheltenham Town | 1:2 | ||||
| 31. Round | 14/02/2004 | Doncaster Rovers | - | Macclesfield Town | 1:0 | |
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| 32. Round | 21/02/2004 | Macclesfield Town | - | Carlisle United | 1:1 | ||||
| 33. Round | 28/02/2004 | Southend United | - | Macclesfield Town | 1:0 | ||||
| 35. Round | 06/03/2004 | Macclesfield Town | - | Darlington FC | 0:1 |
England