| 1. Round | 09/08/2008 | Oldham Athletic | - | Millwall FC | 4:3 |  |
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| 2. Round | 16/08/2008 | Leeds United | - | Oldham Athletic | 0:2 | |
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| 3. Round | 23/08/2008 | Oldham Athletic | - | Cheltenham Town | 4:0 | ||||
| 4. Round | 30/08/2008 | Colchester United | - | Oldham Athletic | 2:2 | ||||
| 5. Round | 06/09/2008 | Tranmere Rovers | - | Oldham Athletic | 0:1 | ||||
| 6. Round | 13/09/2008 | Oldham Athletic | - | Milton Keynes Dons | 2:0 | ||||
| 7. Round | 20/09/2008 | Hartlepool United | - | Oldham Athletic | 3:3 | ||||
| 8. Round | 27/09/2008 | Oldham Athletic | - | Huddersfield Town | 1:1 | ||||
| 9. Round | 03/10/2008 | Stockport County | - | Oldham Athletic | 3:1 | ||||
| 18. Round | 25/11/2008 | Oldham Athletic | - | Walsall FC | 3:2 | ||||
| 19. Round | 06/12/2008 | Oldham Athletic | - | Brighton & Hove Albion | 1:1 | ||||
| 21. Round | 20/12/2008 | Oldham Athletic | - | Leyton Orient | 1:1 | ||||
| 22. Round | 26/12/2008 | Crewe Alexandra | - | Oldham Athletic | 0:3 |
England
