| 2. Round | 10/08/2005 | Boston United | - | Shrewsbury Town | 1:1 | ||||
| 3. Round | 13/08/2005 | Boston United | - | Stockport County | 2:2 | ||||
| 4. Round | 20/08/2005 | Cheltenham Town | - | Boston United | 3:0 | ||||
| 5. Round | 27/08/2005 | Boston United | - | Mansfield Town | 2:2 | ||||
| 6. Round | 29/08/2005 | Northampton Town | - | Boston United | 3:2 | ||||
| 7. Round | 04/09/2005 | Macclesfield Town | - | Boston United | 2:2 |  |
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| 8. Round | 10/09/2005 | Boston United | - | Rochdale AFC | 3:2 | ||||
| 9. Round | 17/09/2005 | Bury FC | - | Boston United | 1:1 | ||||
| 10. Round | 24/09/2005 | Boston United | - | Grimsby Town | 1:1 | ||||
| 11. Round | 27/09/2005 | Darlington FC | - | Boston United | 0:0 | ||||
| 12. Round | 01/10/2005 | Boston United | - | Peterborough United | 1:0 |
England