| Preston North End FC v Chesterfield FC 31/08/1998 | View match | |
| Chesterfield FC v Gillingham FC 05/09/1998 | View match | |
| Bristol Rovers FC v Chesterfield FC 08/09/1998 | View match | |
| Chesterfield FC v Walsall FC 12/09/1998 | View match | |
| Leicester City FC v Chesterfield FC 16/09/1998 | View match | |
| Manchester City FC v Chesterfield FC 19/09/1998 | £6.50 | |
| Chesterfield FC v Leicester City FC 22/09/1998 | View match | |
| Chesterfield FC v Wrexham FC 26/09/1998 | View match | |
| Millwall FC v Chesterfield FC 03/10/1998 | View match | |
| Stoke City FC v Chesterfield FC 12/10/1998 | View match | |
| Chesterfield FC v York City FC 17/10/1998 | View match | |
| Chesterfield FC v Notts County FC 20/10/1998 | View match |