| 2. Jornada | 16.08.2008 | Tranmere Rovers | - | Hartlepool United | 1:0 | ||||
| 4. Jornada | 30.08.2008 | Peterborough United | - | Hartlepool United | 1:2 | ||||
| 5. Jornada | 06.09.2008 | Millwall FC | - | Hartlepool United | 2:0 | ||||
| 6. Jornada | 12.09.2008 | Hartlepool United | - | Cheltenham Town | 4:1 | ||||
| 7. Jornada | 20.09.2008 | Hartlepool United | - | Oldham Athletic | 3:3 | ||||
| 8. Jornada | 27.09.2008 | Leicester City | - | Hartlepool United | 1:0 | ||||
| 9. Jornada | 03.10.2008 | Hartlepool United | - | Swindon Town | 3:3 |  |
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| 20. Jornada | 13.12.2008 | Hereford United | - | Hartlepool United | 1:1 | ||||
| 22. Jornada | 26.12.2008 | Scunthorpe United | - | Hartlepool United | 3:0 | ||||
| 23. Jornada | 28.12.2008 | Hartlepool United | - | Crewe Alexandra | 1:4 | ||||
| 25. Jornada | 12.01.2009 | Oldham Athletic | - | Hartlepool United | 2:1 | ||||
| 26. Jornada | 16.01.2009 | Hartlepool United | - | Northampton Town | 2:0 | ||||
| 29. Jornada | 31.01.2009 | Brighton & Hove Albion | - | Hartlepool United | 2:1 | ||||
| 30. Jornada | 03.02.2009 | Huddersfield Town | - | Hartlepool United | 1:1 | ||||
| 31. Jornada | 07.02.2009 | Hartlepool United | - | Walsall FC | 2:2 |
Escocia