1. Round | 08/08/2009 | Torquay United | - | Chesterfield FC | 2:0 | ||||
4. Round | 22/08/2009 | Shrewsbury Town | - | Chesterfield FC | 1:1 | ||||
9. Round | 26/09/2009 | Bradford City | - | Chesterfield FC | 3:0 | ||||
27. Round | 16/01/2010 | Chesterfield FC | - | Torquay United | 1:0 | ||||
26. Round | 23/01/2010 | Northampton Town | - | Chesterfield FC | 0:0 | ||||
29. Round | 30/01/2010 | Morecambe FC | - | Chesterfield FC | 0:1 | ||||
30. Round | 06/02/2010 | Chesterfield FC | - | Lincoln City | 2:1 | ||||
42. Round | 13/04/2010 | Grimsby Town | - | Chesterfield FC | 2:2 | ||||
43. Round | 17/04/2010 | Macclesfield Town | - | Chesterfield FC | 2:0 |