| 1. Round | 09/08/2008 | Oldham Athletic | - | Millwall FC | 4:3 | ||||
| 5. Round | 06/09/2008 | Tranmere Rovers | - | Oldham Athletic | 0:1 | ||||
| 7. Round | 20/09/2008 | Hartlepool United | - | Oldham Athletic | 3:3 |  |
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| 9. Round | 03/10/2008 | Stockport County | - | Oldham Athletic | 3:1 | ||||
| 10. Round | 12/10/2008 | Oldham Athletic | - | Hereford United | 4:0 | ||||
| 11. Round | 18/10/2008 | Oldham Athletic | - | Leicester City | 1:1 | ||||
| 12. Round | 21/10/2008 | Bristol Rovers | - | Oldham Athletic | 2:0 | ||||
| 13. Round | 25/10/2008 | Swindon Town | - | Oldham Athletic | 2:0 | ||||
| 24. Round | 03/01/2009 | Huddersfield Town | - | Oldham Athletic | 1:1 | ||||
| 25. Round | 12/01/2009 | Oldham Athletic | - | Hartlepool United | 2:1 | ||||
| 26. Round | 17/01/2009 | Hereford United | - | Oldham Athletic | 5:0 | ||||
| 27. Round | 24/01/2009 | Oldham Athletic | - | Stockport County | 3:1 |
England