| Doncaster Rovers FC v Chesterfield FC 18/09/1987 | View match | |
| Chesterfield FC v Notts County FC 26/09/1987 | View match | |
| Bristol City FC v Chesterfield FC 29/09/1987 | View match | |
| Chesterfield FC v Rotherham United FC 03/10/1987 | View match | |
| Chesterfield FC v Grimsby Town FC 10/10/1987 | View match | |
| Northampton Town FC v Chesterfield FC 17/10/1987 | £3.00 | |
| Northampton Town FC v Chesterfield FC 17/10/1987 | £4.00 | |
| Aldershot F.C v Chesterfield FC 20/10/1987 | View match | |
| Chesterfield FC v Southend United FC 24/10/1987 | View match | |
| York City FC v Chesterfield FC 31/10/1987 | View match | |
| Chesterfield FC v Wigan Athletic FC 03/11/1987 | View match | |
| Bristol Rovers FC v Chesterfield FC 07/11/1987 | View match |