| Notts County FC v Chesterfield FC 21/02/1987 | View match | |
| Chesterfield FC v Bolton Wanderers FC 28/02/1987 | View match | |
| Chesterfield FC v Gillingham FC 03/03/1987 | View match | |
| Newport County v Chesterfield FC 08/03/1987 | View match | |
| Chesterfield FC v Swindon Town FC 14/03/1987 | View match | |
| Wigan Athletic FC v Chesterfield FC 17/03/1987 | View match | |
| Port Vale FC v Chesterfield FC 21/03/1987 | View match | |
| Chesterfield FC v Bristol Rovers FC 28/03/1987 | View match | |
| Chesterfield FC v York City FC 04/04/1987 | View match | |
| Fulham FC v Chesterfield FC 11/04/1987 | £0.00 | |
| Walsall FC v Chesterfield FC 14/04/1987 | View match | |
| Chesterfield FC v Brentford FC 18/04/1987 | View match |