| Chesterfield FC v Blackpool FC 09/11/1991 | View match | |
| Darlington FC v Chesterfield FC 16/11/1991 | View match | |
| Wrexham FC v Chesterfield FC 23/11/1991 | View match | |
| Barnet FC v Chesterfield FC 30/11/1991 | View match | |
| Chesterfield FC v Northampton Town FC 21/12/1991 | View match | |
| Maidstone United (Old) v Chesterfield FC 26/12/1991 | View match | |
| Mansfield Town FC v Chesterfield FC 28/12/1991 | View match | |
| Chesterfield FC v Burnley FC 01/01/1992 | View match | |
| Chesterfield FC v Carlisle United FC 04/01/1992 | View match | |
| Bury FC v Chesterfield FC 14/01/1992 | £8.50 | |
| Chesterfield FC v Doncaster Rovers FC 18/01/1992 | View match | |
| Cardiff City FC v Chesterfield FC 25/01/1992 | View match |