| 1. Round | 09/08/2003 | Macclesfield Town | - | Boston United | 0:0 | ||||
| 3. Round | 22/08/2003 | Swansea City | - | Boston United | 3:0 | ||||
| 4. Round | 25/08/2003 | Boston United | - | Carlisle United | 1:0 | ||||
| 7. Round | 13/09/2003 | Bristol Rovers | - | Boston United | 2:0 | ||||
| 8. Round | 17/09/2003 | Boston United | - | Cambridge United | 1:2 |  |
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| 9. Round | 20/09/2003 | Boston United | - | Bury FC | 1:0 | ||||
| 10. Round | 27/09/2003 | Darlington FC | - | Boston United | 3:0 | ||||
| 11. Round | 30/09/2003 | Yeovil Town | - | Boston United | 2:0 | ||||
| 25. Round | 03/01/2004 | Carlisle United | - | Boston United | 2:1 | ||||
| 26. Round | 10/01/2004 | Boston United | - | Macclesfield Town | 3:1 | ||||
| 27. Round | 17/01/2004 | Huddersfield Town | - | Boston United | 2:0 | ||||
| 30. Round | 07/02/2004 | Lincoln City | - | Boston United | 1:1 | |
England
