1. Round | 08/08/2009 | Torquay United | - | Chesterfield FC | 2:0 | ||||
7. Round | 12/09/2009 | Dagenham & Redbridge | - | Chesterfield FC | 2:1 | ||||
8. Round | 19/09/2009 | Chesterfield FC | - | Macclesfield Town | 4:1 | ||||
9. Round | 26/09/2009 | Bradford City | - | Chesterfield FC | 3:0 |