| 7. Round | 12/09/2009 | Leyton Orient | - | Exeter City | 1:1 | ||||
| 8. Round | 19/09/2009 | Stockport County | - | Leyton Orient | 2:1 | ||||
| 9. Round | 26/09/2009 | Leyton Orient | - | Millwall FC | 1:0 |  |
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| 10. Round | 29/09/2009 | Norwich City | - | Leyton Orient | 4:0 | ||||
| 11. Round | 03/10/2009 | Wycombe Wanderers | - | Leyton Orient | 0:1 | |
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| 12. Round | 10/10/2009 | Leyton Orient | - | Colchester United | 0:1 | ||||
| 13. Round | 17/10/2009 | Leyton Orient | - | Brentford FC | 2:1 | ||||
| 14. Round | 24/10/2009 | Huddersfield Town | - | Leyton Orient | 4:0 | ||||
| 22. Round | 19/12/2009 | Walsall FC | - | Leyton Orient | 2:2 | ||||
| 24. Round | 28/12/2009 | Leyton Orient | - | Southend United | 1:2 | ||||
| 34. Round | 27/02/2010 | Leyton Orient | - | Swindon Town | 0:0 | ||||
| 35. Round | 06/03/2010 | Milton Keynes Dons | - | Leyton Orient | 1:0 | ||||
| 36. Round | 13/03/2010 | Leyton Orient | - | Walsall FC | 2:0 | ||||
| 37. Round | 20/03/2010 | Leyton Orient | - | Huddersfield Town | 0:2 | |
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| 40. Round | 05/04/2010 | Southampton FC | - | Leyton Orient | 2:1 | ||||
| 46. Round | 08/05/2010 | Colchester United | - | Leyton Orient | 1:0 |
England