| Chesterfield FC v Blackpool FC 24/09/1988 | View match | |
| Chesterfield FC v Bury FC 01/10/1988 | £5.00 | |
| Notts County FC v Chesterfield FC 04/10/1988 | £4.00 | |
| Gillingham FC v Chesterfield FC 08/10/1988 | View match | |
| Chesterfield FC v Preston North End FC 15/10/1988 | View match | |
| Southend United FC v Chesterfield FC 22/10/1988 | View match | |
| Chesterfield FC v Brentford FC 25/10/1988 | View match | |
| Bolton Wanderers FC v Chesterfield FC 29/10/1988 | View match | |
| Chesterfield FC v Bristol Rovers FC 05/11/1988 | View match | |
| Chester City FC v Chesterfield FC 12/11/1988 | View match | |
| Bolton Wanderers FC v Chesterfield FC 19/11/1988 | View match | |
| Reading FC v Chesterfield FC 26/11/1988 | View match |