| 2. Round | 18/08/2001 | Oldham Athletic | - | Chesterfield FC | 1:1 | ||||
| 3. Round | 25/08/2001 | Chesterfield FC | - | Brentford FC | 0:1 | ||||
| 4. Round | 27/08/2001 | Notts County | - | Chesterfield FC | 1:1 | ||||
| 5. Round | 01/09/2001 | Chesterfield FC | - | Peterborough United | 0:1 | ||||
| 6. Round | 08/09/2001 | Wycombe Wanderers | - | Chesterfield FC | 0:0 | ||||
| 7. Round | 15/09/2001 | Northampton Town | - | Chesterfield FC | 0:2 |  |
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| 8. Round | 18/09/2001 | Chesterfield FC | - | Wrexham AFC | 3:2 | |
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| 9. Round | 22/09/2001 | Chesterfield FC | - | Swindon Town | 4:0 |  |
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| 11. Round | 29/09/2001 | Chesterfield FC | - | Tranmere Rovers | 0:2 |
England