| Chester City FC v Walsall FC 24/11/1989 | View match | |
| Chester City FC v Rochdale FC 28/11/1989 | View match | |
| Shrewsbury Town FC v Chester City FC 02/12/1989 | £4.50 | |
| Blackpool FC v Chester City FC 09/12/1989 | View match | |
| Tranmere Rovers FC v Chester City FC 15/12/1989 | View match | |
| Chester City FC v Wigan Athletic FC 26/12/1989 | View match | |
| Chester City FC v Blackpool FC 30/12/1989 | View match | |
| Northampton Town FC v Chester City FC 01/01/1990 | View match | |
| Chester City FC v Leyton Orient FC 06/01/1990 | View match | |
| Blackpool FC v Chester City FC 10/01/1990 | View match | |
| Chester City FC v Brentford FC 12/01/1990 | View match | |
| Mansfield Town FC v Chester City FC 20/01/1990 | View match |