| 16. Round | 15/11/2008 | Northampton Town | - | Oldham Athletic | 0:1 |  |
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| 17. Round | 22/11/2008 | Southend United | - | Oldham Athletic | 1:2 | ||||
| 18. Round | 25/11/2008 | Oldham Athletic | - | Walsall FC | 3:2 | ||||
| 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 |  |
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| 23. Round | 28/12/2008 | Oldham Athletic | - | Carlisle United | 0:0 | ||||
| 24. Round | 03/01/2009 | Huddersfield Town | - | Oldham Athletic | 1:1 |
England
Jamaica