| Chelsea FC v Derby County FC 16/04/1949 | View match | |
| Chelsea FC v Manchester City FC 18/04/1949 | View match | |
| Arsenal FC v Chelsea FC 23/04/1949 | View match | |
| Heart Of Midlothian (Hearts) v Chelsea FC 27/04/1949 | View match | |
| Chelsea FC v Sunderland FC 30/04/1949 | £7.50 | |
| Bolton Wanderers FC v Chelsea FC 04/05/1949 | View match | |
| Wolverhampton Wanderers FC v Chelsea FC 07/05/1949 | View match | |
| Birmingham City FC v Chelsea FC 20/08/1949 | View match | |
| Chelsea FC v Arsenal FC 24/08/1949 | View match | |
| Chelsea FC v Derby County FC 27/08/1949 | View match | |
| Arsenal FC v Chelsea FC 31/08/1949 | View match | |
| West Bromwich Albion FC v Chelsea FC 03/09/1949 | View match |