| Chesterfield FC v Brentford FC 16/12/1995 | View match | |
| Brighton & Hove Albion FC v Chesterfield FC 22/12/1995 | £4.50 | |
| Brighton & Hove Albion FC v Chesterfield FC 22/12/1995 | £4.00 | |
| Chesterfield FC v Peterborough United FC 26/12/1995 | View match | |
| Carlisle United FC v Chesterfield FC 13/01/1996 | View match | |
| Chesterfield FC v Oxford United FC 20/01/1996 | View match | |
| Chesterfield FC v Swansea City FC 03/02/1996 | View match | |
| Chesterfield FC v Wycombe Wanderers FC 17/02/1996 | View match | |
| Rotherham United FC v Chesterfield FC 24/02/1996 | View match | |
| Peterborough United FC v Chesterfield FC 02/03/1996 | View match | |
| Wrexham FC v Chesterfield FC 05/03/1996 | View match | |
| Chesterfield FC v Brighton & Hove Albion FC 09/03/1996 | £6.50 |