1. Round | 08/08/2009 | Torquay United | - | Chesterfield FC | 2:0 | ||||
21. Round | 12/12/2009 | Chesterfield FC | - | Cheltenham Town | 1:0 | ||||
23. Round | 26/12/2009 | Lincoln City | - | Chesterfield FC | 2:1 | ||||
25. Round | 02/01/2010 | Chesterfield FC | - | Shrewsbury Town | 0:1 |