| 1. Round | 09/08/2003 | Leyton Orient | - | Doncaster Rovers | 1:3 | ||||
| 2. Round | 16/08/2003 | Mansfield Town | - | Leyton Orient | 1:1 | ||||
| 3. Round | 23/08/2003 | Leyton Orient | - | Yeovil Town | 2:0 | ||||
| 4. Round | 25/08/2003 | Darlington FC | - | Leyton Orient | 2:1 | ||||
| 6. Round | 06/09/2003 | Torquay United | - | Leyton Orient | 2:1 | ||||
| 7. Round | 13/09/2003 | Lincoln City | - | Leyton Orient | 0:0 | ||||
| 8. Round | 16/09/2003 | Leyton Orient | - | Hull City | 1:1 |  |
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| 9. Round | 20/09/2003 | Leyton Orient | - | Scunthorpe United | 1:1 | ||||
| 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 | |
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| 15. Round | 21/10/2003 | Bristol Rovers | - | Leyton Orient | 1:1 | ||||
| 16. Round | 25/10/2003 | Leyton Orient | - | Northampton Town | 1:1 |
Wales