| Chesterfield FC v Southend United FC 27/08/1960 | View match | |
| Bury FC v Chesterfield FC 30/08/1960 | £7.50 | |
| Port Vale FC v Chesterfield FC 03/09/1960 | View match | |
| Chesterfield FC v Halifax Town A.F.C 05/09/1960 | View match | |
| Chesterfield FC v Torquay United FC 10/09/1960 | View match | |
| Halifax Town A.F.C v Chesterfield FC 12/09/1960 | View match | |
| Swindon Town FC v Chesterfield FC 17/09/1960 | View match | |
| Walsall FC v Chesterfield FC 20/09/1960 | View match | |
| Chesterfield FC v Brentford FC 24/09/1960 | View match | |
| Chesterfield FC v Walsall FC 26/09/1960 | View match | |
| Watford FC v Chesterfield FC 01/10/1960 | View match | |
| Reading FC v Chesterfield FC 08/10/1960 | View match |