| Chesterfield FC v Northampton Town FC 27/08/2002 | View match | |
| Luton Town FC v Chesterfield FC 31/08/2002 | £5.00 | |
| Crewe Alexandra FC v Chesterfield FC 07/09/2002 | View match | |
| Grimsby Town FC v Chesterfield FC 10/09/2002 | View match | |
| Chesterfield FC v Wigan Athletic FC 14/09/2002 | View match | |
| Chesterfield FC v Stockport County FC 17/09/2002 | View match | |
| Plymouth Argyle FC v Chesterfield FC 21/09/2002 | View match | |
| Chesterfield FC v Blackpool FC 28/09/2002 | View match | |
| Chesterfield FC v West Ham United FC 01/10/2002 | £6.50 | |
| Bristol City FC v Chesterfield FC 05/10/2002 | View match | |
| Chesterfield FC v Tranmere Rovers FC 12/10/2002 | View match | |
| Colchester United FC v Chesterfield FC 18/10/2002 | View match |