| 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 | |
| Chesterfield FC v Macclesfield Town FC 30/09/2000 | View match | |
| Chesterfield FC v Plymouth Argyle FC 07/10/2000 | View match | |
| Exeter City FC v Chesterfield FC 14/10/2000 | View match | |
| Rochdale FC v Chesterfield FC 17/10/2000 | View match | |
| Chesterfield FC v Brighton & Hove Albion FC 21/10/2000 | £5.00 | |
| Kidderminister Harriers v Chesterfield FC 24/10/2000 | View match | |
| Chesterfield FC v Cardiff City FC 28/10/2000 | View match | |
| Lincoln City FC v Chesterfield FC 04/11/2000 | View match |