| 29. Round | 31/01/2009 | Brighton & Hove Albion | - | Hartlepool United | 2:1 | ||||
| 30. Round | 03/02/2009 | Huddersfield Town | - | Hartlepool United | 1:1 |  |
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| 33. Round | 21/02/2009 | Hartlepool United | - | Leyton Orient | 0:1 | ||||
| 27. Round | 24/02/2009 | Swindon Town | - | Hartlepool United | 0:1 | ||||
| 39. Round | 21/03/2009 | Hartlepool United | - | Millwall FC | 2:3 | ||||
| 40. Round | 27/03/2009 | Southend United | - | Hartlepool United | 3:2 |  |
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| 41. Round | 04/04/2009 | Hartlepool United | - | Hereford United | 4:2 | ||||
| 42. Round | 11/04/2009 | Crewe Alexandra | - | Hartlepool United | 0:0 | ||||
| 43. Round | 13/04/2009 | Hartlepool United | - | Scunthorpe United | 2:3 |  |
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| 44. Round | 18/04/2009 | Yeovil Town | - | Hartlepool United | 2:3 | |
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| 45. Round | 25/04/2009 | Hartlepool United | - | Leeds United | 0:1 | ||||
| 46. Round | 02/05/2009 | Bristol Rovers | - | Hartlepool United | 4:1 | |
England