| 9. Round | 03/10/2008 | Hartlepool United | - | Swindon Town | 3:3 | ||||
| 10. Round | 10/10/2008 | Northampton Town | - | Hartlepool United | 1:0 | ||||
| 11. Round | 18/10/2008 | Walsall FC | - | Hartlepool United | 2:3 | ||||
| 12. Round | 21/10/2008 | Hartlepool United | - | Huddersfield Town | 5:3 |  |
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| 13. Round | 25/10/2008 | Hartlepool United | - | Brighton & Hove Albion | 1:0 | |
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| 14. Round | 28/10/2008 | Carlisle United | - | Hartlepool United | 0:1 | ||||
| 15. Round | 01/11/2008 | Leyton Orient | - | Hartlepool United | 1:0 | |
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| 16. Round | 15/11/2008 | Hartlepool United | - | Milton Keynes Dons | 1:3 | ||||
| 17. Round | 22/11/2008 | Leeds United | - | Hartlepool United | 4:1 | ||||
| 18. Round | 25/11/2008 | Hartlepool United | - | Bristol Rovers | 1:1 | ||||
| 19. Round | 06/12/2008 | Hartlepool United | - | Yeovil Town | 0:0 | ||||
| 20. Round | 13/12/2008 | Hereford United | - | Hartlepool United | 1:1 | |
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| 21. Round | 19/12/2008 | Hartlepool United | - | Southend United | 3:0 | |
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| 22. Round | 26/12/2008 | Scunthorpe United | - | Hartlepool United | 3:0 | |
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| 23. Round | 28/12/2008 | Hartlepool United | - | Crewe Alexandra | 1:4 |
Scotland