| Chelsea FC v Arsenal FC 22/03/1950 | View match | |
| Portsmouth FC v Chelsea FC 25/03/1950 | View match | |
| Chelsea FC v Middlesbrough FC 29/03/1950 | View match | |
| Chelsea FC v Huddersfield Town FC 01/04/1950 | View match | |
| Chelsea FC v Bolton Wanderers FC 07/04/1950 | £15.00 | |
| Aston Villa FC v Chelsea FC 08/04/1950 | View match | |
| Bolton Wanderers FC v Chelsea FC 10/04/1950 | View match | |
| Chelsea FC v Wolverhampton Wanderers FC 15/04/1950 | View match | |
| Brentford FC v Chelsea FC 17/04/1950 | View match | |
| Blackpool FC v Chelsea FC 22/04/1950 | View match | |
| Chelsea FC v Heart Of Midlothian (Hearts) 26/04/1950 | View match | |
| Chelsea FC v Heart Of Midlothian (Hearts) 26/04/1950 | View match |