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 |