| 20. Round | 13/12/2008 | Hereford United | - | Hartlepool United | 1:1 | ||||
| 22. Round | 26/12/2008 | Scunthorpe United | - | Hartlepool United | 3:0 |  |
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| 25. Round | 12/01/2009 | Oldham Athletic | - | Hartlepool United | 2:1 | ||||
| 26. Round | 16/01/2009 | Hartlepool United | - | Northampton Town | 2:0 | ||||
| 32. Round | 14/02/2009 | Milton Keynes Dons | - | Hartlepool United | 3:1 | ||||
| 46. Round | 02/05/2009 | Bristol Rovers | - | Hartlepool United | 4:1 |
England
Belgium