| 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 | |
| Doncaster Rovers FC v Chesterfield FC 20/04/1987 | View match | |
| Chesterfield FC v Chester City FC 25/04/1987 | View match | |
| Bury FC v Chesterfield FC 02/05/1987 | View match | |
| Chesterfield FC v Darlington FC 04/05/1987 | View match | |
| Carlisle United FC v Chesterfield FC 09/05/1987 | View match | |
| Preston North End FC v Chesterfield FC 15/08/1987 | View match | |
| Chesterfield FC v Peterborough United FC 18/08/1987 | View match | |
| Chesterfield FC v Brighton & Hove Albion FC 22/08/1987 | £6.50 | |
| Peterborough United FC v Chesterfield FC 26/08/1987 | View match |