| Newport County v Chesterfield FC 12/04/1986 | View match | |
| Chesterfield FC v Bristol Rovers FC 15/04/1986 | View match | |
| Chesterfield FC v Brentford FC 19/04/1986 | View match | |
| Darlington FC v Chesterfield FC 22/04/1986 | View match | |
| Bristol Rovers FC v Chesterfield FC 26/04/1986 | £9.50 | |
| Chesterfield FC v Bolton Wanderers FC 03/08/1986 | View match | |
| Blackpool FC v Chesterfield FC 23/08/1986 | View match | |
| Chesterfield FC v Wrexham FC 26/08/1986 | View match | |
| Chesterfield FC v Walsall FC 30/08/1986 | View match | |
| Wrexham FC v Chesterfield FC 02/09/1986 | View match | |
| Mansfield Town FC v Chesterfield FC 07/09/1986 | View match | |
| Chesterfield FC v Bristol City FC 13/09/1986 | View match |