| Wolverhampton Wanderers FC v Chester City FC 02/01/1989 | View match | |
| Fulham FC v Chester City FC 07/01/1989 | £4.00 | |
| Chester City FC v Port Vale FC 14/01/1989 | View match | |
| Bristol City FC v Chester City FC 21/01/1989 | View match | |
| Chester City FC v Reading FC 04/02/1989 | View match | |
| Brentford FC v Chester City FC 11/02/1989 | View match | |
| Chester City FC v Notts County FC 18/02/1989 | View match | |
| Mansfield Town FC v Chester City FC 28/02/1989 | View match | |
| Chester City FC v Bristol Rovers FC 04/03/1989 | View match | |
| Swansea City FC v Chester City FC 11/03/1989 | View match | |
| Chester City FC v Aldershot F.C 15/03/1989 | View match | |
| Blackpool FC v Chester City FC 18/03/1989 | View match |