1. Round | 08/08/2009 | Torquay United | - | Chesterfield FC | 2:0 | ||||
3. Round | 19/08/2009 | Chesterfield FC | - | Notts County | 2:1 | ||||
4. Round | 22/08/2009 | Shrewsbury Town | - | Chesterfield FC | 1:1 | ||||
10. Round | 30/09/2009 | Chesterfield FC | - | Grimsby Town | 3:2 | ||||
12. Round | 10/10/2009 | AFC Bournemouth | - | Chesterfield FC | 1:2 | ||||
13. Round | 17/10/2009 | Hereford United | - | Chesterfield FC | 1:0 | ||||
14. Round | 24/10/2009 | Chesterfield FC | - | Burton Albion | 5:2 | ||||
42. Round | 13/04/2010 | Grimsby Town | - | Chesterfield FC | 2:2 | ||||
43. Round | 17/04/2010 | Macclesfield Town | - | Chesterfield FC | 2:0 | ||||
46. Round | 08/05/2010 | Chesterfield FC | - | AFC Bournemouth | 2:1 |