| 1. Round | 08/08/2009 | Milton Keynes Dons | - | Hartlepool United | 0:0 | ||||
| 2. Round | 15/08/2009 | Hartlepool United | - | Charlton Athletic | 0:2 | ||||
| 3. Round | 18/08/2009 | Hartlepool United | - | Bristol Rovers | 1:2 |  |
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| 4. Round | 22/08/2009 | Gillingham FC | - | Hartlepool United | 0:1 | ||||
| 5. Round | 29/08/2009 | Hartlepool United | - | Norwich City | 0:2 | ||||
| 6. Round | 04/09/2009 | Oldham Athletic | - | Hartlepool United | 0:3 | ||||
| 7. Round | 12/09/2009 | Hartlepool United | - | Wycombe Wanderers | 1:1 | ||||
| 8. Round | 19/09/2009 | Colchester United | - | Hartlepool United | 2:0 | ||||
| 11. Round | 03/10/2009 | Exeter City | - | Hartlepool United | 3:1 | ||||
| 26. Round | 19/01/2010 | Charlton Athletic | - | Hartlepool United | 2:1 | ||||
| 28. Round | 23/01/2010 | Bristol Rovers | - | Hartlepool United | 2:0 | ||||
| 39. Round | 03/04/2010 | Leyton Orient | - | Hartlepool United | 1:3 | ||||
| 40. Round | 05/04/2010 | Hartlepool United | - | Brighton & Hove Albion | 2:0 | |
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| 41. Round | 10/04/2010 | Wycombe Wanderers | - | Hartlepool United | 2:0 | ||||
| 42. Round | 13/04/2010 | Hartlepool United | - | Stockport County | 3:0 |
England