| Chesterfield FC v Scunthorpe United FC 23/10/1999 | View match | |
| Chesterfield FC v Enfield 30/10/1999 | View match | |
| Wigan Athletic FC v Chesterfield FC 02/11/1999 | View match | |
| Chesterfield FC v Oldham Athletic FC 06/11/1999 | View match | |
| Cardiff City FC v Chesterfield FC 12/11/1999 | View match | |
| Chesterfield FC v Bristol Rovers FC 20/11/1999 | View match | |
| Chesterfield FC v Oxford United FC 27/11/1999 | View match | |
| Colchester United FC v Chesterfield FC 03/12/1999 | View match | |
| Chesterfield FC v Bristol City FC 07/12/1999 | View match | |
| Brentford FC v Chesterfield FC 10/12/1999 | View match | |
| Luton Town FC v Chesterfield FC 26/12/1999 | £6.00 | |
| Chesterfield FC v Bury FC 28/12/1999 | £6.50 |