| Hartlepool United v Chesterfield FC 19/08/2000 | View match | |
| Port Vale FC v Chesterfield FC 22/08/2000 | View match | |
| Chesterfield FC v Shrewsbury Town FC 26/08/2000 | View match | |
| Scunthorpe United FC v Chesterfield FC 28/08/2000 | View match | |
| Chesterfield FC v Barnet FC 02/09/2000 | View match | |
| Chesterfield FC v Port Vale FC 05/09/2000 | View match | |
| Cheltenham Town FC v Chesterfield FC 09/09/2000 | View match | |
| Carlisle United FC v Chesterfield FC 12/09/2000 | View match | |
| Chesterfield FC v Mansfield Town FC 16/09/2000 | View match | |
| Chesterfield FC v Fulham FC 19/09/2000 | View match | |
| Blackpool FC v Chesterfield FC 23/09/2000 | View match | |
| Fulham FC v Chesterfield FC 27/09/2000 | £4.50 |