13. Round | 25/10/2008 | Yeovil Town | - | Leyton Orient | 0:0 | ||||
14. Round | 28/10/2008 | Leyton Orient | - | Milton Keynes Dons | 1:2 | ||||
15. Round | 01/11/2008 | Leyton Orient | - | Hartlepool United | 1:0 | ||||
16. Round | 15/11/2008 | Crewe Alexandra | - | Leyton Orient | 0:2 | ||||
17. Round | 22/11/2008 | Leyton Orient | - | Millwall FC | 0:0 | ||||
18. Round | 25/11/2008 | Huddersfield Town | - | Leyton Orient | 0:1 | ||||
19. Round | 06/12/2008 | Northampton Town | - | Leyton Orient | 1:1 | ||||
20. Round | 13/12/2008 | Leyton Orient | - | Cheltenham Town | 1:2 | ||||
21. Round | 20/12/2008 | Oldham Athletic | - | Leyton Orient | 1:1 | ||||
22. Round | 26/12/2008 | Leyton Orient | - | Swindon Town | 1:2 | ||||
23. Round | 28/12/2008 | Colchester United | - | Leyton Orient | 1:0 | ||||
25. Round | 10/01/2009 | Leicester City | - | Leyton Orient | 3:0 | ||||
26. Round | 17/01/2009 | Leyton Orient | - | Bristol Rovers | 1:2 |