| 22. Round | 26/12/2008 | Crewe Alexandra | - | Oldham Athletic | 0:3 | ||||
| 23. Round | 28/12/2008 | Oldham Athletic | - | Carlisle United | 0:0 | ||||
| 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 | ||||
| 45. Round | 25/04/2009 | Oldham Athletic | - | Southend United | 1:1 | ||||
| 46. Round | 02/05/2009 | Walsall FC | - | Oldham Athletic | 1:2 |
England
