1. Jornada | 09.08.2008 | Barnet FC | - | Chesterfield FC | 1:3 | ||||
2. Jornada | 16.08.2008 | Chesterfield FC | - | Bury FC | 1:3 | ||||
3. Jornada | 23.08.2008 | Grimsby Town | - | Chesterfield FC | 0:1 | ||||
4. Jornada | 30.08.2008 | Chesterfield FC | - | Wycombe Wanderers | 0:1 | ||||
6. Jornada | 13.09.2008 | Dagenham & Redbridge | - | Chesterfield FC | 3:0 | ||||
7. Jornada | 20.09.2008 | Rochdale AFC | - | Chesterfield FC | 2:1 | ||||
8. Jornada | 27.09.2008 | Chesterfield FC | - | Brentford FC | 0:1 | ||||
9. Jornada | 04.10.2008 | Morecambe FC | - | Chesterfield FC | 2:2 | ||||
11. Jornada | 18.10.2008 | Lincoln City | - | Chesterfield FC | 3:1 | ||||
13. Jornada | 25.10.2008 | Chesterfield FC | - | Notts County | 3:1 | ||||
14. Jornada | 28.10.2008 | Exeter City | - | Chesterfield FC | 1:6 | ||||
15. Jornada | 01.11.2008 | Bournemouth | - | Chesterfield FC | 1:1 | ||||
17. Jornada | 22.11.2008 | Chesterfield FC | - | Accrington Stanley | 1:1 | ||||
20. Jornada | 12.12.2008 | Chesterfield FC | - | Macclesfield Town | 2:4 | ||||
21. Jornada | 20.12.2008 | Port Vale FC | - | Chesterfield FC | 0:1 | ||||
22. Jornada | 26.12.2008 | Chesterfield FC | - | Luton Town | 2:2 | ||||
27. Jornada | 24.01.2009 | Chesterfield FC | - | Morecambe FC | 1:2 |