| 9. Jornada | 03.10.2008 | Hartlepool United | - | Swindon Town | 3:3 | ||||
| 10. Jornada | 10.10.2008 | Northampton Town | - | Hartlepool United | 1:0 | ||||
| 11. Jornada | 18.10.2008 | Walsall FC | - | Hartlepool United | 2:3 | ||||
| 12. Jornada | 21.10.2008 | Hartlepool United | - | Huddersfield Town | 5:3 |  |
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| 13. Jornada | 25.10.2008 | Hartlepool United | - | Brighton & Hove Albion | 1:0 | |
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| 14. Jornada | 28.10.2008 | Carlisle United | - | Hartlepool United | 0:1 | ||||
| 15. Jornada | 01.11.2008 | Leyton Orient | - | Hartlepool United | 1:0 | |
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| 16. Jornada | 15.11.2008 | Hartlepool United | - | Milton Keynes Dons | 1:3 | ||||
| 17. Jornada | 22.11.2008 | Leeds United | - | Hartlepool United | 4:1 | ||||
| 18. Jornada | 25.11.2008 | Hartlepool United | - | Bristol Rovers | 1:1 | ||||
| 19. Jornada | 06.12.2008 | Hartlepool United | - | Yeovil Town | 0:0 | ||||
| 20. Jornada | 13.12.2008 | Hereford United | - | Hartlepool United | 1:1 | |
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| 21. Jornada | 19.12.2008 | Hartlepool United | - | Southend United | 3:0 | |
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| 22. Jornada | 26.12.2008 | Scunthorpe United | - | Hartlepool United | 3:0 | |
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| 23. Jornada | 28.12.2008 | Hartlepool United | - | Crewe Alexandra | 1:4 |
Escocia