| Chesterfield FC v Burnley FC 21/09/1996 | View match | |
| Bristol Rovers FC v Chesterfield FC 28/09/1996 | View match | |
| Chesterfield FC v Shrewsbury Town FC 01/10/1996 | View match | |
| Chesterfield FC v Bristol City FC 05/10/1996 | View match | |
| Millwall FC v Chesterfield FC 12/10/1996 | View match | |
| Notts County FC v Chesterfield FC 15/10/1996 | View match | |
| Chesterfield FC v Crewe Alexandra FC 19/10/1996 | View match | |
| Chesterfield FC v York City FC 26/10/1996 | View match | |
| Stockport County FC v Chesterfield FC 29/10/1996 | View match | |
| Wrexham FC v Chesterfield FC 02/11/1996 | View match | |
| Chesterfield FC v Preston North End FC 09/11/1996 | View match | |
| Chesterfield FC v Bury FC 16/11/1996 | £5.00 |