| 13. Round | 11/10/2003 | Boston United | - | Cheltenham Town | 3:1 | ||||
| 14. Round | 18/10/2003 | York City | - | Boston United | 1:1 | ||||
| 15. Round | 21/10/2003 | Southend United | - | Boston United | 0:2 | ||||
| 16. Round | 25/10/2003 | Boston United | - | Torquay United | 4:0 | ||||
| 17. Round | 01/11/2003 | Mansfield Town | - | Boston United | 2:1 | ||||
| 21. Round | 13/12/2003 | Boston United | - | Northampton Town | 1:1 | ||||
| 22. Round | 20/12/2003 | Rochdale AFC | - | Boston United | 1:0 | ||||
| 23. Round | 26/12/2003 | Boston United | - | Lincoln City | 0:1 | ||||
| 25. Round | 03/01/2004 | Carlisle United | - | Boston United | 2:1 | ||||
| 30. Round | 07/02/2004 | Lincoln City | - | Boston United | 1:1 |  |
England