| 26. Round | 17/01/2009 | Wycombe Wanderers | - | Grimsby Town | 0:1 | ||||
| 27. Round | 24/01/2009 | Grimsby Town | - | Rotherham United | 3:0 |  |
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| 28. Round | 27/01/2009 | Grimsby Town | - | Dagenham & Redbridge | 1:1 | ||||
| 29. Round | 31/01/2009 | Bradford City | - | Grimsby Town | 2:0 | ||||
| 31. Round | 07/02/2009 | Grimsby Town | - | Exeter City | 2:2 | ||||
| 24. Round | 10/02/2009 | Barnet FC | - | Grimsby Town | 3:3 |  |
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| 33. Round | 21/02/2009 | Darlington FC | - | Grimsby Town | 1:0 | ||||
| 25. Round | 24/02/2009 | Grimsby Town | - | Morecambe FC | 2:3 | ||||
| 34. Round | 28/02/2009 | Rochdale AFC | - | Grimsby Town | 2:0 |
England