26. Round | 17/01/2009 | Chester City | - | Chesterfield FC | 1:3 | ||||
27. Round | 24/01/2009 | Chesterfield FC | - | Morecambe FC | 1:2 | ||||
28. Round | 28/01/2009 | Chesterfield FC | - | Exeter City | 2:1 | ||||
29. Round | 31/01/2009 | Notts County | - | Chesterfield FC | 0:1 | ||||
32. Round | 14/02/2009 | Shrewsbury Town | - | Chesterfield FC | 2:1 | ||||
33. Round | 20/02/2009 | Chesterfield FC | - | AFC Bournemouth | 1:0 | ||||
38. Round | 14/03/2009 | Chesterfield FC | - | Dagenham & Redbridge | 1:1 | ||||
39. Round | 21/03/2009 | Rotherham United | - | Chesterfield FC | 3:0 | ||||
25. Round | 25/03/2009 | Chesterfield FC | - | Rochdale AFC | 3:0 | ||||
40. Round | 28/03/2009 | Chesterfield FC | - | Port Vale FC | 2:1 | ||||
30. Round | 31/03/2009 | Aldershot Town | - | Chesterfield FC | 1:1 | ||||
31. Round | 07/04/2009 | Chesterfield FC | - | Lincoln City | 1:1 | ||||
42. Round | 11/04/2009 | Chesterfield FC | - | Darlington FC | 0:0 | ||||
43. Round | 13/04/2009 | Luton Town | - | Chesterfield FC | 0:0 | ||||
44. Round | 18/04/2009 | Chesterfield FC | - | Gillingham FC | 0:1 | ||||
46. Round | 02/05/2009 | Chesterfield FC | - | Bradford City | 0:2 |