| 16. Round | 14/11/2008 | Chesterfield FC | - | Shrewsbury Town | 2:2 | ||||
| 17. Round | 22/11/2008 | Lincoln City | - | Shrewsbury Town | 0:0 | ||||
| 18. Round | 25/11/2008 | Shrewsbury Town | - | Dagenham & Redbridge | 2:1 |  |
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| 19. Round | 06/12/2008 | Shrewsbury Town | - | Rotherham United | 1:0 | ||||
| 20. Round | 13/12/2008 | Grimsby Town | - | Shrewsbury Town | 1:0 | ||||
| 21. Round | 20/12/2008 | Shrewsbury Town | - | Wycombe Wanderers | 0:1 | ||||
| 22. Round | 26/12/2008 | Rochdale AFC | - | Shrewsbury Town | 2:1 | ||||
| 23. Round | 28/12/2008 | Shrewsbury Town | - | Bury FC | 1:0 | ||||
| 24. Round | 03/01/2009 | Bradford City | - | Shrewsbury Town | 0:0 |
England