| 1. Round | 09/08/2008 | Hartlepool United | - | Colchester United | 4:2 | ||||
| 2. Round | 16/08/2008 | Tranmere Rovers | - | Hartlepool United | 1:0 | ||||
| 3. Round | 23/08/2008 | Hartlepool United | - | Stockport County | 0:1 | ||||
| 4. Round | 30/08/2008 | Peterborough United | - | Hartlepool United | 1:2 |  |
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| 5. Round | 06/09/2008 | Millwall FC | - | Hartlepool United | 2:0 | ||||
| 6. Round | 12/09/2008 | Hartlepool United | - | Cheltenham Town | 4:1 | ||||
| 7. Round | 20/09/2008 | Hartlepool United | - | Oldham Athletic | 3:3 | ||||
| 8. Round | 27/09/2008 | Leicester City | - | Hartlepool United | 1:0 |
England