| 1. Round | 09/08/2003 | Macclesfield Town | - | Boston United | 0:0 |  |
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| 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 | ||||
| 6. Round | 06/09/2003 | Mansfield Town | - | Macclesfield Town | 3:2 | ||||
| 7. Round | 13/09/2003 | Macclesfield Town | - | Kidderminster Harriers | 1:1 | ||||
| 8. Round | 16/09/2003 | Swansea City | - | Macclesfield Town | 3:0 | ||||
| 28. Round | 24/01/2004 | Torquay United | - | Macclesfield Town | 4:1 | ||||
| 35. Round | 06/03/2004 | Macclesfield Town | - | Darlington FC | 0:1 |
England