| 4. Round | 30/08/2008 | Hereford United | - | Crewe Alexandra | 2:0 | ||||
| 5. Round | 06/09/2008 | Leeds United | - | Crewe Alexandra | 5:2 | ||||
| 8. Round | 27/09/2008 | Bristol Rovers | - | Crewe Alexandra | 0:0 | ||||
| 10. Round | 11/10/2008 | Scunthorpe United | - | Crewe Alexandra | 3:0 |  |
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| 13. Round | 24/10/2008 | Tranmere Rovers | - | Crewe Alexandra | 2:0 | ||||
| 14. Round | 28/10/2008 | Crewe Alexandra | - | Peterborough United | 1:1 | ||||
| 15. Round | 01/11/2008 | Huddersfield Town | - | Crewe Alexandra | 3:2 | ||||
| 33. Round | 21/02/2009 | Crewe Alexandra | - | Huddersfield Town | 3:1 | ||||
| 30. Round | 24/02/2009 | Crewe Alexandra | - | Yeovil Town | 2:0 | ||||
| 34. Round | 28/02/2009 | Brighton & Hove Albion | - | Crewe Alexandra | 0:4 |  |
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| 35. Round | 03/03/2009 | Crewe Alexandra | - | Carlisle United | 1:2 | ||||
| 37. Round | 10/03/2009 | Walsall FC | - | Crewe Alexandra | 1:1 | |
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| 38. Round | 14/03/2009 | Colchester United | - | Crewe Alexandra | 0:1 | ||||
| 24. Round | 17/03/2009 | Crewe Alexandra | - | Bristol Rovers | 1:1 | ||||
| 39. Round | 21/03/2009 | Crewe Alexandra | - | Leeds United | 2:3 |
England