| 30. Round | 06/02/2010 | Chesterfield FC | - | Lincoln City | 2:1 | ||||
| 22. Round | 09/02/2010 | Port Vale FC | - | Chesterfield FC | 1:2 | ||||
| 31. Round | 13/02/2010 | Chesterfield FC | - | Bury FC | 1:0 | ||||
| 32. Round | 20/02/2010 | Darlington FC | - | Chesterfield FC | 2:3 |  |
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| 33. Round | 24/02/2010 | Crewe Alexandra | - | Chesterfield FC | 0:1 | ||||
| 34. Round | 27/02/2010 | Chesterfield FC | - | Aldershot Town | 0:1 | ||||
| 35. Round | 06/03/2010 | Cheltenham Town | - | Chesterfield FC | 0:1 | ||||
| 36. Round | 13/03/2010 | Chesterfield FC | - | Port Vale FC | 0:5 | ||||
| 37. Round | 20/03/2010 | Burton Albion | - | Chesterfield FC | 2:2 | ||||
| 38. Round | 27/03/2010 | Chesterfield FC | - | Hereford United | 1:2 | ||||
| 39. Round | 03/04/2010 | Chesterfield FC | - | Rochdale AFC | 2:0 | |
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| 40. Round | 05/04/2010 | Barnet FC | - | Chesterfield FC | 3:1 | ||||
| 41. Round | 10/04/2010 | Chesterfield FC | - | Dagenham & Redbridge | 2:2 | ||||
| 44. Round | 24/04/2010 | Chesterfield FC | - | Bradford City | 1:1 | ||||
| 45. Round | 01/05/2010 | Accrington Stanley | - | Chesterfield FC | 2:0 | ||||
| 46. Round | 08/05/2010 | Chesterfield FC | - | AFC Bournemouth | 2:1 |
England