| Chesterfield FC v Cardiff City FC 21/03/2000 | View match | |
| Chesterfield FC v Luton Town FC 25/03/2000 | View match | |
| Chesterfield FC v Bury FC 28/03/2000 | View match | |
| Gillingham FC v Chesterfield FC 01/04/2000 | View match | |
| Chesterfield FC v Wycombe Wanderers FC 08/04/2000 | View match | |
| Bury FC v Chesterfield FC 15/04/2000 | £6.00 | |
| Oldham Athletic FC v Chesterfield FC 18/04/2000 | View match | |
| Chesterfield FC v Wrexham FC 22/04/2000 | View match | |
| AFC Bournemouth v Chesterfield FC 25/04/2000 | View match | |
| Chesterfield FC v Notts County FC 29/04/2000 | View match | |
| Blackpool FC v Chesterfield FC 06/05/2000 | View match | |
| Chesterfield FC v York City FC 12/08/2000 | View match |