1. Round | 09/08/2008 | Barnet FC | - | Chesterfield FC | 1:3 | ||||
2. Round | 16/08/2008 | Chesterfield FC | - | Bury FC | 1:3 | ||||
3. Round | 23/08/2008 | Grimsby Town | - | Chesterfield FC | 0:1 | ||||
4. Round | 30/08/2008 | Chesterfield FC | - | Wycombe Wanderers | 0:1 | ||||
7. Round | 20/09/2008 | Rochdale AFC | - | Chesterfield FC | 2:1 | ||||
8. Round | 27/09/2008 | Chesterfield FC | - | Brentford FC | 0:1 | ||||
9. Round | 04/10/2008 | Morecambe FC | - | Chesterfield FC | 2:2 | ||||
19. Round | 06/12/2008 | Gillingham FC | - | Chesterfield FC | 2:1 | ||||
21. Round | 20/12/2008 | Port Vale FC | - | Chesterfield FC | 0:1 | ||||
22. Round | 26/12/2008 | Chesterfield FC | - | Luton Town | 2:2 | ||||
23. Round | 28/12/2008 | Darlington FC | - | Chesterfield FC | 0:0 |