40. Round | 27/03/2009 | Southend United | - | Hartlepool United | 3:2 | ||||
41. Round | 04/04/2009 | Hartlepool United | - | Hereford United | 4:2 | ||||
42. Round | 11/04/2009 | Crewe Alexandra | - | Hartlepool United | 0:0 | ||||
43. Round | 13/04/2009 | Hartlepool United | - | Scunthorpe United | 2:3 | ||||
44. Round | 18/04/2009 | Yeovil Town | - | Hartlepool United | 2:3 | ||||
45. Round | 25/04/2009 | Hartlepool United | - | Leeds United | 0:1 | ||||
46. Round | 02/05/2009 | Bristol Rovers | - | Hartlepool United | 4:1 |