| 1. Round | 10/08/2002 | Queens Park Rangers | - | Chesterfield FC | 3:1 | ||||
| 2. Round | 13/08/2002 | Chesterfield FC | - | Swindon Town | 2:4 | ||||
| 3. Round | 17/08/2002 | Chesterfield FC | - | Port Vale FC | 2:1 | ||||
| 6. Round | 31/08/2002 | Luton Town | - | Chesterfield FC | 3:0 | ||||
| 7. Round | 07/09/2002 | Crewe Alexandra | - | Chesterfield FC | 0:0 | ||||
| 15. Round | 26/10/2002 | Chesterfield FC | - | Notts County | 0:0 | ||||
| 17. Round | 02/11/2002 | Chesterfield FC | - | Barnsley FC | 1:0 | ||||
| 18. Round | 09/11/2002 | Peterborough United | - | Chesterfield FC | 1:0 |  |
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| 34. Round | 01/03/2003 | Wigan Athletic | - | Chesterfield FC | 3:1 |
England