| Orient v Chester City FC 19/04/1986 | View match | |
| Chester City FC v Southend United FC 26/04/1986 | View match | |
| Rochdale FC v Chester City FC 29/04/1986 | View match | |
| Scunthorpe United FC v Chester City FC 03/05/1986 | View match | |
| Chester City FC v Carlisle United FC 23/08/1986 | View match | |
| Derby County FC v Chester City FC 27/08/1986 | View match | |
| Bury FC v Chester City FC 30/08/1986 | £5.00 | |
| Chester City FC v Derby County FC 03/09/1986 | View match | |
| Chester City FC v Fulham FC 06/09/1986 | View match | |
| Swindon Town FC v Chester City FC 13/09/1986 | View match | |
| AFC Bournemouth v Chester City FC 16/09/1986 | View match | |
| Darlington FC v Chester City FC 27/09/1986 | View match |