| Barnsley FC v Chesterfield FC 15/04/1961 | View match | |
| Chesterfield FC v Reading FC 22/04/1961 | View match | |
| Tranmere Rovers FC v Chesterfield FC 24/04/1961 | View match | |
| Colchester United FC v Chesterfield FC 29/04/1961 | View match | |
| Chesterfield FC v Rotherham United FC 12/08/1961 | View match | |
| Chesterfield FC v Workington 19/08/1961 | View match | |
| Exeter City FC v Chesterfield FC 23/08/1961 | £7.00 | |
| York City FC v Chesterfield FC 26/08/1961 | View match | |
| Chesterfield FC v Exeter City FC 28/08/1961 | View match | |
| Aldershot F.C v Chesterfield FC 02/09/1961 | View match | |
| Crewe Alexandra FC v Chesterfield FC 06/09/1961 | View match | |
| Chesterfield FC v Gillingham FC 09/09/1961 | View match |