| 19. Round | 06/12/2008 | Port Vale FC | - | Grimsby Town | 2:1 | ||||
| 20. Round | 13/12/2008 | Bury FC | - | Port Vale FC | 3:0 | ||||
| 21. Round | 20/12/2008 | Port Vale FC | - | Chesterfield FC | 0:1 | ||||
| 22. Round | 26/12/2008 | Rotherham United | - | Port Vale FC | 1:0 | ||||
| 23. Round | 28/12/2008 | Port Vale FC | - | Rochdale AFC | 2:1 |  |
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| 26. Round | 17/01/2009 | Port Vale FC | - | Shrewsbury Town | 1:1 | |
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| 24. Round | 20/01/2009 | Port Vale FC | - | Gillingham FC | 1:3 | ||||
| 27. Round | 24/01/2009 | Notts County | - | Port Vale FC | 4:2 | ||||
| 28. Round | 27/01/2009 | Port Vale FC | - | Chester City | 3:0 | ||||
| 33. Round | 20/02/2009 | Port Vale FC | - | Lincoln City | 0:1 | ||||
| 38. Round | 14/03/2009 | Port Vale FC | - | Darlington FC | 3:1 | ||||
| 35. Round | 17/03/2009 | Accrington Stanley | - | Port Vale FC | 2:0 | ||||
| 41. Round | 04/04/2009 | Port Vale FC | - | Bury FC | 1:1 | ||||
| 43. Round | 13/04/2009 | Port Vale FC | - | Rotherham United | 0:0 | ||||
| 44. Round | 18/04/2009 | Grimsby Town | - | Port Vale FC | 3:0 | ||||
| 45. Round | 25/04/2009 | Port Vale FC | - | Wycombe Wanderers | 1:1 | ||||
| 46. Round | 02/05/2009 | Barnet FC | - | Port Vale FC | 1:2 |
England