| Luton Town FC v Chesterfield FC 26/12/1999 | £6.00 | |
| Wycombe Wanderers FC v Chesterfield FC 03/01/2000 | View match | |
| Chesterfield FC v Brentford FC 08/01/2000 | View match | |
| Chesterfield FC v Burnley FC 15/01/2000 | View match | |
| Cambridge United FC v Chesterfield FC 22/01/2000 | View match | |
| Chesterfield FC v Millwall FC 29/01/2000 | View match | |
| Chesterfield FC v Gillingham FC 01/02/2000 | View match | |
| Bristol City FC v Chesterfield FC 05/02/2000 | View match | |
| Chesterfield FC v Preston North End FC 12/02/2000 | View match | |
| Oxford United FC v Chesterfield FC 19/02/2000 | View match | |
| Chesterfield FC v Reading FC 26/02/2000 | View match | |
| Stoke City FC v Chesterfield FC 04/03/2000 | View match |