| York City FC v Chesterfield FC 08/11/1986 | View match | |
| Walsall FC v Chesterfield FC 15/11/1986 | View match | |
| AFC Bournemouth v Chesterfield FC 22/11/1986 | View match | |
| Chesterfield FC v Bury FC 29/11/1986 | £4.50 | |
| Chesterfield FC v Middlesbrough FC 02/12/1986 | View match | |
| Doncaster Rovers FC v Chesterfield FC 09/12/1986 | View match | |
| Chesterfield FC v Carlisle United FC 13/12/1986 | View match | |
| Chester City FC v Chesterfield FC 19/12/1986 | View match | |
| Chesterfield FC v Doncaster Rovers FC 26/12/1986 | View match | |
| Darlington FC v Chesterfield FC 27/12/1986 | View match | |
| Brentford FC v Chesterfield FC 01/01/1987 | View match | |
| Chesterfield FC v AFC Bournemouth 03/01/1987 | View match |