| 1. Round | 08/08/2009 | Crewe Alexandra | - | Dagenham & Redbridge | 1:2 | ||||
| 2. Round | 15/08/2009 | Grimsby Town | - | Crewe Alexandra | 0:4 |  |
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| 3. Round | 18/08/2009 | Darlington FC | - | Crewe Alexandra | 0:1 | ||||
| 4. Round | 22/08/2009 | Crewe Alexandra | - | Hereford United | 1:0 | |
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| 5. Round | 29/08/2009 | AFC Bournemouth | - | Crewe Alexandra | 1:0 | |
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| 6. Round | 05/09/2009 | Crewe Alexandra | - | Macclesfield Town | 2:1 | ||||
| 7. Round | 12/09/2009 | Shrewsbury Town | - | Crewe Alexandra | 2:0 | ||||
| 8. Round | 19/09/2009 | Crewe Alexandra | - | Aldershot Town | 1:2 | ||||
| 9. Round | 25/09/2009 | Accrington Stanley | - | Crewe Alexandra | 5:3 | ||||
| 10. Round | 29/09/2009 | Crewe Alexandra | - | Bury FC | 2:3 |  |
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| 13. Round | 17/10/2009 | Crewe Alexandra | - | Port Vale FC | 1:2 |
England