6. Round | 13/09/2008 | Dagenham & Redbridge | - | Chesterfield FC | 3:0 | ||||
22. Round | 26/12/2008 | Chesterfield FC | - | Luton Town | 2:2 | ||||
23. Round | 28/12/2008 | Darlington FC | - | Chesterfield FC | 0:0 | ||||
32. Round | 14/02/2009 | Shrewsbury Town | - | Chesterfield FC | 2:1 | ||||
37. Round | 11/03/2009 | Chesterfield FC | - | Grimsby Town | 2:1 | ||||
40. Round | 28/03/2009 | Chesterfield FC | - | Port Vale FC | 2:1 | ||||
30. Round | 31/03/2009 | Aldershot Town | - | Chesterfield FC | 1:1 | ||||
42. Round | 11/04/2009 | Chesterfield FC | - | Darlington FC | 0:0 | ||||
44. Round | 18/04/2009 | Chesterfield FC | - | Gillingham FC | 0:1 | ||||
45. Round | 25/04/2009 | Accrington Stanley | - | Chesterfield FC | 1:0 | ||||
46. Round | 02/05/2009 | Chesterfield FC | - | Bradford City | 0:2 |