| Fulham FC v Chesterfield FC 19/12/1987 | £3.50 | |
| Notts County FC v Chesterfield FC 26/12/1987 | View match | |
| Chesterfield FC v Walsall FC 28/12/1987 | View match | |
| Chesterfield FC v Mansfield Town FC 01/01/1988 | View match | |
| Port Vale FC v Chesterfield FC 02/01/1988 | View match | |
| Chesterfield FC v Doncaster Rovers FC 16/01/1988 | View match | |
| Halifax Town A.F.C v Chesterfield FC 19/01/1988 | View match | |
| Bury FC v Chesterfield FC 30/01/1988 | View match | |
| Chesterfield FC v Gillingham FC 06/02/1988 | View match | |
| Walsall FC v Chesterfield FC 13/02/1988 | View match | |
| Brighton & Hove Albion FC v Chesterfield FC 17/02/1988 | £4.50 | |
| Brighton & Hove Albion FC v Chesterfield FC 17/02/1988 | £3.50 |