| 10. Round | 27/09/2003 | Huddersfield Town | - | Leyton Orient | 3:0 | ||||
| 11. Round | 30/09/2003 | Carlisle United | - | Leyton Orient | 0:1 | ||||
| 12. Round | 04/10/2003 | Leyton Orient | - | Macclesfield Town | 2:0 |  |
|||
| 13. Round | 11/10/2003 | Leyton Orient | - | Swansea City | 1:2 | ||||
| 14. Round | 18/10/2003 | Southend United | - | Leyton Orient | 1:2 | ||||
| 15. Round | 21/10/2003 | Bristol Rovers | - | Leyton Orient | 1:1 | ||||
| 16. Round | 25/10/2003 | Leyton Orient | - | Northampton Town | 1:1 | ||||
| 17. Round | 01/11/2003 | Leyton Orient | - | Rochdale AFC | 2:1 | ||||
| 18. Round | 15/11/2003 | Boston United | - | Leyton Orient | 3:0 | ||||
| 37. Round | 16/03/2004 | Hull City | - | Leyton Orient | 3:0 |
England