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 | ||||
5. Round | 06/09/2008 | Chesterfield FC | - | Rotherham United | 1:0 | ||||
6. Round | 13/09/2008 | Dagenham & Redbridge | - | Chesterfield FC | 3:0 | ||||
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 | ||||
13. Round | 25/10/2008 | Chesterfield FC | - | Notts County | 3:1 | ||||
14. Round | 28/10/2008 | Exeter City | - | Chesterfield FC | 1:6 | ||||
15. Round | 01/11/2008 | AFC Bournemouth | - | Chesterfield FC | 1:1 | ||||
16. Round | 14/11/2008 | Chesterfield FC | - | Shrewsbury Town | 2:2 | ||||
17. Round | 22/11/2008 | Chesterfield FC | - | Accrington Stanley | 1:1 | ||||
18. Round | 25/11/2008 | Bradford City | - | Chesterfield FC | 3:2 | ||||
19. Round | 06/12/2008 | Gillingham FC | - | Chesterfield FC | 2:1 | ||||
20. Round | 12/12/2008 | Chesterfield FC | - | Macclesfield Town | 2:4 |