| 29. Ronde | 31.01.2009 | Brighton & Hove Albion | - | Hartlepool United | 2:1 | ||||
| 30. Ronde | 03.02.2009 | Huddersfield Town | - | Hartlepool United | 1:1 |  |
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| 33. Ronde | 21.02.2009 | Hartlepool United | - | Leyton Orient | 0:1 | ||||
| 27. Ronde | 24.02.2009 | Swindon Town | - | Hartlepool United | 0:1 | ||||
| 39. Ronde | 21.03.2009 | Hartlepool United | - | Millwall FC | 2:3 | ||||
| 40. Ronde | 27.03.2009 | Southend United | - | Hartlepool United | 3:2 |  |
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| 41. Ronde | 04.04.2009 | Hartlepool United | - | Hereford United | 4:2 | ||||
| 42. Ronde | 11.04.2009 | Crewe Alexandra | - | Hartlepool United | 0:0 | ||||
| 43. Ronde | 13.04.2009 | Hartlepool United | - | Scunthorpe United | 2:3 |  |
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| 44. Ronde | 18.04.2009 | Yeovil Town | - | Hartlepool United | 2:3 | |
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| 45. Ronde | 25.04.2009 | Hartlepool United | - | Leeds United | 0:1 | ||||
| 46. Ronde | 02.05.2009 | Bristol Rovers | - | Hartlepool United | 4:1 | |
Engeland