| Chesterfield FC v Brighton & Hove Albion FC 22/08/1987 | £6.50 | |
| Peterborough United FC v Chesterfield FC 26/08/1987 | View match | |
| Mansfield Town FC v Chesterfield FC 29/08/1987 | View match | |
| Chesterfield FC v Bury FC 31/08/1987 | £5.50 | |
| Gillingham FC v Chesterfield FC 05/09/1987 | View match | |
| Chesterfield FC v Port Vale FC 12/09/1987 | View match | |
| Brentford FC v Chesterfield FC 15/09/1987 | View match | |
| 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 |