8. Round | 27/09/2008 | Chesterfield FC | - | Brentford FC | 0:1 | ||||
10. Round | 11/10/2008 | Chesterfield FC | - | Chester City | 1:1 | ||||
11. Round | 18/10/2008 | Lincoln City | - | Chesterfield FC | 3:1 | ||||
12. Round | 22/10/2008 | Chesterfield FC | - | Aldershot Town | 5:1 | ||||
19. Round | 06/12/2008 | Gillingham FC | - | Chesterfield FC | 2:1 |