| 39. Round | 21/03/2009 | Grimsby Town | - | Gillingham FC | 3:0 |  |
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| 40. Round | 28/03/2009 | Grimsby Town | - | Aldershot Town | 1:0 | |
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| 41. Round | 04/04/2009 | Shrewsbury Town | - | Grimsby Town | 1:1 | |
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| 42. Round | 11/04/2009 | Grimsby Town | - | Accrington Stanley | 0:1 | ||||
| 43. Round | 13/04/2009 | Notts County | - | Grimsby Town | 0:2 | ||||
| 44. Round | 18/04/2009 | Grimsby Town | - | Port Vale FC | 3:0 | |
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| 45. Round | 25/04/2009 | AFC Bournemouth | - | Grimsby Town | 2:1 | ||||
| 46. Round | 02/05/2009 | Grimsby Town | - | Macclesfield Town | 0:0 |
Ireland