| 1. Round | 08/11/2008 | Brighton & Hove Albion | - | Hartlepool United | 3:3 | ||||
| 1. Round | 18/11/2008 | Hartlepool United | - | Brighton & Hove Albion | 2:1 | ||||
| 2. Round | 29/11/2008 | Fleetwood Town | - | Hartlepool United | 2:3 | ||||
| 3. Round | 03/01/2009 | Hartlepool United | - | Stoke City | 2:0 |  |
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| 4. Round | 24/01/2009 | Hartlepool United | - | West Ham United | 0:2 |
England