| Chesterfield FC v Swindon Town FC 23/04/1996 | View match | |
| AFC Bournemouth v Chesterfield FC 27/04/1996 | View match | |
| York City FC v Chesterfield FC 30/04/1996 | View match | |
| Chesterfield FC v Notts County FC 04/05/1996 | View match | |
| Chesterfield FC v Notts County FC 04/05/1996 | View match | |
| Blackpool FC v Chesterfield FC 17/08/1996 | View match | |
| Stockport County FC v Chesterfield FC 20/08/1996 | View match | |
| Chesterfield FC v Bury FC 24/08/1996 | £5.00 | |
| Chesterfield FC v Walsall FC 27/08/1996 | View match | |
| Gillingham FC v Chesterfield FC 31/08/1996 | View match | |
| Chesterfield FC v Stockport County FC 03/09/1996 | View match | |
| Chesterfield FC v Brentford FC 07/09/1996 | View match |