| 1. Round | 09/08/2003 | Macclesfield Town | - | Boston United | 0:0 | ||||
| 2. Round | 16/08/2003 | Boston United | - | Huddersfield Town | 2:2 | ||||
| 3. Round | 22/08/2003 | Swansea City | - | Boston United | 3:0 |  |
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| 4. Round | 25/08/2003 | Boston United | - | Carlisle United | 1:0 | ||||
| 5. Round | 30/08/2003 | Hull City | - | Boston United | 2:1 | ||||
| 20. Round | 29/11/2003 | Boston United | - | Kidderminster Harriers | 2:2 | |
England