| Hull City FC v Chesterfield FC 14/01/1950 | View match | |
| Chesterfield FC v Brentford FC 21/01/1950 | View match | |
| Chesterfield FC v Middlesbrough FC 28/01/1950 | View match | |
| Blackburn Rovers FC v Chesterfield FC 04/02/1950 | View match | |
| Chesterfield FC v Chelsea FC 11/02/1950 | View match | |
| Chelsea FC v Chesterfield FC 15/02/1950 | View match | |
| Chesterfield FC v Cardiff City FC 18/02/1950 | View match | |
| Chesterfield FC v West Ham United FC 25/02/1950 | View match | |
| Sheffield United FC v Chesterfield FC 04/03/1950 | View match | |
| Chesterfield FC v Grimsby Town FC 11/03/1950 | View match | |
| Queens Park Rangers FC v Chesterfield FC 18/03/1950 | £16.99 | |
| Queens Park Rangers FC v Chesterfield FC 18/03/1950 | £11.99 |