1. Round | 09/08/2008 | Leyton Orient | - | Hereford United | 2:1 | ||||
2. Round | 16/08/2008 | Peterborough United | - | Leyton Orient | 3:0 | ||||
3. Round | 23/08/2008 | Leyton Orient | - | Carlisle United | 0:0 | ||||
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 | ||||
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 |