| 31. Jornada | 07.02.2009 | Tranmere Rovers | - | Leyton Orient | 0:0 | ||||
| 32. Jornada | 14.02.2009 | Leyton Orient | - | Crewe Alexandra | 1:0 |  |
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| 33. Jornada | 21.02.2009 | Hartlepool United | - | Leyton Orient | 0:1 | ||||
| 34. Jornada | 28.02.2009 | Hereford United | - | Leyton Orient | 2:1 | ||||
| 35. Jornada | 03.03.2009 | Leyton Orient | - | Peterborough United | 2:3 | ||||
| 37. Jornada | 10.03.2009 | Carlisle United | - | Leyton Orient | 1:3 | ||||
| 38. Jornada | 14.03.2009 | Stockport County | - | Leyton Orient | 0:1 | ||||
| 39. Jornada | 21.03.2009 | Leyton Orient | - | Walsall FC | 0:1 | ||||
| 40. Jornada | 28.03.2009 | Leyton Orient | - | Oldham Athletic | 2:1 | ||||
| 41. Jornada | 04.04.2009 | Cheltenham Town | - | Leyton Orient | 0:1 | ||||
| 30. Jornada | 07.04.2009 | Leyton Orient | - | Leeds United | 2:2 | ||||
| 42. Jornada | 11.04.2009 | Leyton Orient | - | Colchester United | 2:1 |  |
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| 43. Jornada | 13.04.2009 | Swindon Town | - | Leyton Orient | 0:1 | ||||
| 44. Jornada | 18.04.2009 | Leyton Orient | - | Northampton Town | 1:3 | ||||
| 45. Jornada | 25.04.2009 | Millwall FC | - | Leyton Orient | 2:1 | ||||
| 46. Jornada | 02.05.2009 | Leyton Orient | - | Huddersfield Town | 1:1 |
Inglaterra