| 9. Round | 20/09/2014 | Scunthorpe United | - | Leyton Orient | 1:2 | ||||
| 10. Round | 27/09/2014 | Leyton Orient | - | Rochdale AFC | 2:3 | ||||
| 11. Round | 04/10/2014 | Leyton Orient | - | Swindon Town | 1:2 | ||||
| 12. Round | 11/10/2014 | Sheffield United | - | Leyton Orient | 2:2 | ||||
| 13. Round | 18/10/2014 | Leyton Orient | - | Milton Keynes Dons | 0:0 | ||||
| 14. Round | 21/10/2014 | Doncaster Rovers | - | Leyton Orient | 0:2 | ||||
| 15. Round | 25/10/2014 | Port Vale FC | - | Leyton Orient | 3:0 | ||||
| 6. Round | 28/10/2014 | Leyton Orient | - | Preston North End | 0:2 | ||||
| 16. Round | 01/11/2014 | Leyton Orient | - | Coventry City | 2:2 |  |
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| 20. Round | 13/12/2014 | Leyton Orient | - | Peterborough United | 1:2 |  |
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| 21. Round | 20/12/2014 | Barnsley FC | - | Leyton Orient | 2:0 | ||||
| 22. Round | 26/12/2014 | Leyton Orient | - | Crawley Town | 4:1 | ||||
| 30. Round | 10/02/2015 | Leyton Orient | - | Notts County | 0:1 | ||||
| 31. Round | 14/02/2015 | Chesterfield FC | - | Leyton Orient | 2:3 | ||||
| 44. Round | 18/04/2015 | Milton Keynes Dons | - | Leyton Orient | 6:1 | ||||
| 45. Round | 25/04/2015 | Leyton Orient | - | Sheffield United | 1:1 | |
England