| 8. Round | 27/09/2008 | Oldham Athletic | - | Huddersfield Town | 1:1 | ||||
| 16. Round | 15/11/2008 | Northampton Town | - | Oldham Athletic | 0:1 | ||||
| 17. Round | 22/11/2008 | Southend United | - | Oldham Athletic | 1:2 |  |
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| 18. Round | 25/11/2008 | Oldham Athletic | - | Walsall FC | 3:2 | ||||
| 19. Round | 06/12/2008 | Oldham Athletic | - | Brighton & Hove Albion | 1:1 | ||||
| 20. Round | 13/12/2008 | Peterborough United | - | Oldham Athletic | 2:2 | ||||
| 21. Round | 20/12/2008 | Oldham Athletic | - | Leyton Orient | 1:1 | ||||
| 22. Round | 26/12/2008 | Crewe Alexandra | - | Oldham Athletic | 0:3 | ||||
| 39. Round | 21/03/2009 | Oldham Athletic | - | Tranmere Rovers | 0:2 |  |
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| 40. Round | 28/03/2009 | Leyton Orient | - | Oldham Athletic | 2:1 | ||||
| 42. Round | 10/04/2009 | Carlisle United | - | Oldham Athletic | 1:1 | ||||
| 43. Round | 13/04/2009 | Oldham Athletic | - | Crewe Alexandra | 1:1 | ||||
| 44. Round | 18/04/2009 | Brighton & Hove Albion | - | Oldham Athletic | 3:1 |
Netherlands