| Southampton FC v Chesterfield FC 01/04/1950 | £20.00 | |
| Chesterfield FC v Bradford Park Avenue 07/04/1950 | View match | |
| Chesterfield FC v Coventry City FC 08/04/1950 | View match | |
| Bradford Park Avenue v Chesterfield FC 11/04/1950 | View match | |
| Swansea Town v Chesterfield FC 15/04/1950 | View match | |
| Chesterfield FC v Leeds United FC 22/04/1950 | View match | |
| Luton Town FC v Chesterfield FC 29/04/1950 | View match | |
| Queens Park Rangers FC v Chesterfield FC 19/08/1950 | £32.99 | |
| Chesterfield FC v Grimsby Town FC 21/08/1950 | View match | |
| Chesterfield FC v Barnsley FC 26/08/1950 | View match | |
| Grimsby Town FC v Chesterfield FC 30/08/1950 | View match | |
| Chesterfield FC v Leicester City FC 02/09/1950 | View match |