| 1. Round | 09/08/2008 | Grimsby Town | - | Rochdale AFC | 0:0 | ||||
| 2. Round | 16/08/2008 | Brentford FC | - | Grimsby Town | 4:0 | ||||
| 3. Round | 23/08/2008 | Grimsby Town | - | Chesterfield FC | 0:1 | ||||
| 4. Round | 30/08/2008 | Lincoln City | - | Grimsby Town | 1:1 | ||||
| 5. Round | 06/09/2008 | Gillingham FC | - | Grimsby Town | 3:0 | ||||
| 6. Round | 13/09/2008 | Grimsby Town | - | Chester City | 1:3 |  |
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| 8. Round | 27/09/2008 | Grimsby Town | - | Barnet FC | 0:1 | ||||
| 12. Round | 21/10/2008 | Grimsby Town | - | Luton Town | 2:2 | ||||
| 13. Round | 24/10/2008 | Grimsby Town | - | Bradford City | 1:3 | ||||
| 14. Round | 28/10/2008 | Dagenham & Redbridge | - | Grimsby Town | 4:0 | ||||
| 15. Round | 01/11/2008 | Grimsby Town | - | Darlington FC | 1:2 |  |
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| 16. Round | 15/11/2008 | Bury FC | - | Grimsby Town | 0:2 | ||||
| 17. Round | 21/11/2008 | Grimsby Town | - | AFC Bournemouth | 3:3 | ||||
| 32. Round | 14/02/2009 | Grimsby Town | - | Bury FC | 1:2 | ||||
| 30. Round | 17/03/2009 | Luton Town | - | Grimsby Town | 2:1 |
England