| 18. Round | 15/11/2003 | Boston United | - | Leyton Orient | 3:0 | ||||
| 19. Round | 22/11/2003 | Doncaster Rovers | - | Boston United | 3:0 |  |
|||
| 20. Round | 29/11/2003 | Boston United | - | Kidderminster Harriers | 2:2 |  |
|||
| 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 | ||||
| 24. Round | 28/12/2003 | Scunthorpe United | - | Boston United | 0:1 | ||||
| 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 | ||||
| 31. Round | 14/02/2004 | Cheltenham Town | - | Boston United | 1:0 | ||||
| 28. Round | 18/02/2004 | Boston United | - | Swansea City | 1:1 | |
|||
| 32. Round | 21/02/2004 | Boston United | - | York City | 2:0 |
England