| 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 | ||||
| 23. Round | 21/12/2001 | Brighton & Hove Albion | - | Chesterfield FC | 2:2 | ||||
| 25. Round | 29/12/2001 | Chesterfield FC | - | Notts County | 2:1 | ||||
| 30. Round | 21/01/2002 | Chesterfield FC | - | Brighton & Hove Albion | 1:2 |
England