| 6. Round | 08/09/2001 | Wycombe Wanderers | - | Chesterfield FC | 0:0 |  |
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| 7. Round | 15/09/2001 | Northampton Town | - | Chesterfield FC | 0:2 | ||||
| 8. Round | 18/09/2001 | Chesterfield FC | - | Wrexham AFC | 3:2 | ||||
| 9. Round | 22/09/2001 | Chesterfield FC | - | Swindon Town | 4:0 |  |
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| 10. Round | 25/09/2001 | Huddersfield Town | - | Chesterfield FC | 0:0 | ||||
| 11. Round | 29/09/2001 | Chesterfield FC | - | Tranmere Rovers | 0:2 | ||||
| 12. Round | 05/10/2001 | Bristol City | - | Chesterfield FC | 3:0 | ||||
| 13. Round | 13/10/2001 | Chesterfield FC | - | Port Vale FC | 1:1 | |
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| 14. Round | 20/10/2001 | Bury FC | - | Chesterfield FC | 2:1 | |
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| 15. Round | 23/10/2001 | Chesterfield FC | - | Stoke City | 1:2 | |
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| 16. Round | 27/10/2001 | Blackpool FC | - | Chesterfield FC | 1:0 | |
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| 17. Round | 03/11/2001 | Chesterfield FC | - | Cambridge United | 2:0 | ||||
| 22. Round | 15/12/2001 | Chesterfield FC | - | Queens Park Rangers | 2:3 | ||||
| 29. Round | 19/01/2002 | Colchester United | - | Chesterfield FC | 1:2 |
England