| 33. Round | 21/02/2009 | Hartlepool United | - | Leyton Orient | 0:1 |  |
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| 27. Round | 24/02/2009 | Swindon Town | - | Hartlepool United | 0:1 | ||||
| 34. Round | 28/02/2009 | Colchester United | - | Hartlepool United | 1:1 | ||||
| 35. Round | 03/03/2009 | Hartlepool United | - | Tranmere Rovers | 2:1 |
England