| 2. Round | 16/08/2008 | Carlisle United | - | Crewe Alexandra | 4:2 | ||||
| 18. Round | 25/11/2008 | Leicester City | - | Crewe Alexandra | 2:1 | ||||
| 19. Round | 06/12/2008 | Cheltenham Town | - | Crewe Alexandra | 1:0 | ||||
| 21. Round | 20/12/2008 | Millwall FC | - | Crewe Alexandra | 0:0 | ||||
| 22. Round | 26/12/2008 | Crewe Alexandra | - | Oldham Athletic | 0:3 | ||||
| 23. Round | 28/12/2008 | Hartlepool United | - | Crewe Alexandra | 1:4 | ||||
| 26. Round | 17/01/2009 | Crewe Alexandra | - | Scunthorpe United | 3:2 | ||||
| 27. Round | 24/01/2009 | Northampton Town | - | Crewe Alexandra | 5:1 |  |
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| 28. Round | 27/01/2009 | Peterborough United | - | Crewe Alexandra | 4:2 | ||||
| 29. Round | 31/01/2009 | Crewe Alexandra | - | Tranmere Rovers | 2:1 | ||||
| 25. Round | 17/02/2009 | Southend United | - | Crewe Alexandra | 0:1 | ||||
| 34. Round | 28/02/2009 | Brighton & Hove Albion | - | Crewe Alexandra | 0:4 | |
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| 36. Round | 07/03/2009 | Crewe Alexandra | - | Hereford United | 2:1 |
England