| 8. Jornada | 26.09.2008 | Southend United | - | Leyton Orient | 3:0 | ||||
| 9. Jornada | 04.10.2008 | Leyton Orient | - | Scunthorpe United | 2:2 | ||||
| 10. Jornada | 11.10.2008 | Bristol Rovers | - | Leyton Orient | 2:1 | ||||
| 11. Jornada | 18.10.2008 | Leyton Orient | - | Tranmere Rovers | 0:1 | ||||
| 21. Jornada | 20.12.2008 | Oldham Athletic | - | Leyton Orient | 1:1 | ||||
| 23. Jornada | 28.12.2008 | Colchester United | - | Leyton Orient | 1:0 |  |
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| 25. Jornada | 10.01.2009 | Leicester City | - | Leyton Orient | 3:0 | ||||
| 24. Jornada | 20.01.2009 | Leyton Orient | - | Southend United | 1:1 | ||||
| 27. Jornada | 24.01.2009 | Scunthorpe United | - | Leyton Orient | 2:1 | ||||
| 28. Jornada | 27.01.2009 | Milton Keynes Dons | - | Leyton Orient | 1:2 | ||||
| 34. Jornada | 28.02.2009 | Hereford United | - | Leyton Orient | 2:1 | ||||
| 35. Jornada | 03.03.2009 | Leyton Orient | - | Peterborough United | 2:3 | ||||
| 30. Jornada | 07.04.2009 | Leyton Orient | - | Leeds United | 2:2 |
Inglaterra