| 14. Round | 20/10/2001 | Bury FC | - | Chesterfield FC | 2:1 | ||||
| 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 | ||||
| 17. Round | 03/11/2001 | Chesterfield FC | - | Cambridge United | 2:0 | ||||
| 18. Round | 10/11/2001 | Cardiff City | - | Chesterfield FC | 2:1 |  |
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| 19. Round | 20/11/2001 | Wigan Athletic | - | Chesterfield FC | 1:1 | |
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| 20. Round | 24/11/2001 | Chesterfield FC | - | AFC Bournemouth | 2:1 | |
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| 21. Round | 01/12/2001 | Reading FC | - | Chesterfield FC | 0:1 | ||||
| 22. Round | 15/12/2001 | Chesterfield FC | - | Queens Park Rangers | 2:3 | ||||
| 36. Round | 26/02/2002 | Swindon Town | - | Chesterfield FC | 2:1 | ||||
| 31. Round | 19/03/2002 | Chesterfield FC | - | Bristol City | 2:1 | ||||
| 42. Round | 30/03/2002 | Chesterfield FC | - | Cardiff City | 0:2 | ||||
| 43. Round | 02/04/2002 | Cambridge United | - | Chesterfield FC | 4:1 | ||||
| 44. Round | 06/04/2002 | Chesterfield FC | - | Wigan Athletic | 1:2 |
Wales