| Luton Town FC v Chesterfield FC 31/10/1998 | £6.00 | |
| Chesterfield FC v Lincoln City FC 07/11/1998 | View match | |
| Chesterfield FC v AFC Bournemouth 10/11/1998 | View match | |
| Wycombe Wanderers FC v Chesterfield FC 14/11/1998 | View match | |
| Fulham FC v Chesterfield FC 21/11/1998 | £3.00 | |
| Chesterfield FC v Macclesfield Town FC 28/11/1998 | View match | |
| Blackpool FC v Chesterfield FC 05/12/1998 | View match | |
| Northampton Town FC v Chesterfield FC 12/12/1998 | View match | |
| Chesterfield FC v Wigan Athletic FC 19/12/1998 | View match | |
| Chesterfield FC v Oldham Athletic FC 26/12/1998 | View match | |
| Wycombe Wanderers FC v Chesterfield FC 28/12/1998 | View match | |
| Reading FC v Chesterfield FC 02/01/1999 | View match |