| 3. Round | 16/08/2016 | Leyton Orient | - | Stevenage FC | 3:0 | ||||
| 8. Round | 17/09/2016 | Leyton Orient | - | Yeovil Town | 0:1 | ||||
| 9. Round | 24/09/2016 | Notts County | - | Leyton Orient | 3:1 | ||||
| 10. Round | 27/09/2016 | Leyton Orient | - | Plymouth Argyle | 0:2 | ||||
| 11. Round | 01/10/2016 | Barnet FC | - | Leyton Orient | 0:0 | ||||
| 12. Round | 08/10/2016 | Leyton Orient | - | Portsmouth FC | 0:1 | ||||
| 13. Round | 15/10/2016 | Leyton Orient | - | Luton Town | 1:2 | ||||
| 15. Round | 29/10/2016 | Leyton Orient | - | Crewe Alexandra | 0:2 | ||||
| 16. Round | 12/11/2016 | Colchester United | - | Leyton Orient | 0:3 |  |
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| 17. Round | 19/11/2016 | Leyton Orient | - | Blackpool FC | 1:2 | ||||
| 18. Round | 22/11/2016 | Leyton Orient | - | Exeter City | 0:1 | ||||
| 19. Round | 26/11/2016 | Doncaster Rovers | - | Leyton Orient | 3:1 | ||||
| 20. Round | 10/12/2016 | Leyton Orient | - | Accrington Stanley | 1:0 | |
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| 21. Round | 17/12/2016 | Wycombe Wanderers | - | Leyton Orient | 1:0 |
England
Jamaica