| 19. Round | 01/12/2009 | Carlisle United | - | Hartlepool United | 3:2 | ||||
| 20. Round | 05/12/2009 | Hartlepool United | - | Millwall FC | 3:0 | ||||
| 21. Round | 12/12/2009 | Southend United | - | Hartlepool United | 3:2 |  |
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| 23. Round | 26/12/2009 | Leeds United | - | Hartlepool United | 3:1 | ||||
| 24. Round | 02/01/2010 | Hartlepool United | - | Oldham Athletic | 2:1 | ||||
| 27. Round | 16/01/2010 | Hartlepool United | - | Milton Keynes Dons | 0:5 | ||||
| 37. Round | 19/03/2010 | Tranmere Rovers | - | Hartlepool United | 0:0 | ||||
| 31. Round | 23/03/2010 | Southampton FC | - | Hartlepool United | 3:2 | ||||
| 38. Round | 27/03/2010 | Hartlepool United | - | Swindon Town | 0:1 | ||||
| 41. Round | 10/04/2010 | Wycombe Wanderers | - | Hartlepool United | 2:0 | ||||
| 42. Round | 13/04/2010 | Hartlepool United | - | Stockport County | 3:0 |
England