| 1. Round | 10/08/2002 | Queens Park Rangers | - | Chesterfield FC | 3:1 | ||||
| 2. Round | 13/08/2002 | Chesterfield FC | - | Swindon Town | 2:4 | ||||
| 4. Round | 24/08/2002 | Mansfield Town | - | Chesterfield FC | 0:2 | ||||
| 5. Round | 27/08/2002 | Chesterfield FC | - | Northampton Town | 4:0 | ||||
| 6. Round | 31/08/2002 | Luton Town | - | Chesterfield FC | 3:0 | ||||
| 34. Round | 01/03/2003 | Wigan Athletic | - | Chesterfield FC | 3:1 | ||||
| 38. Round | 18/03/2003 | Chesterfield FC | - | Colchester United | 0:4 | ||||
| 41. Round | 05/04/2003 | Huddersfield Town | - | Chesterfield FC | 4:0 | ||||
| 45. Round | 26/04/2003 | Chesterfield FC | - | Bristol City | 2:0 |  |
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| 46. Round | 03/05/2003 | Blackpool FC | - | Chesterfield FC | 1:1 | |
Scotland