| Arsenal FC v Chelsea FC 31/08/1949 | View match | |
| West Bromwich Albion FC v Chelsea FC 03/09/1949 | View match | |
| Chelsea FC v Sunderland FC 07/09/1949 | View match | |
| Chelsea FC v Manchester United FC 10/09/1949 | View match | |
| Fulham FC v Chelsea FC 17/09/1949 | View match | |
| Stoke City FC v Chelsea FC 24/09/1949 | View match | |
| Chelsea FC v Burnley FC 01/10/1949 | View match | |
| Chelsea FC v Manchester City FC 08/10/1949 | View match | |
| Charlton Athletic FC v Chelsea FC 15/10/1949 | £18.00 | |
| Chelsea FC v Aston Villa FC 22/10/1949 | View match | |
| Wolverhampton Wanderers FC v Chelsea FC 29/10/1949 | View match | |
| Chelsea FC v Portsmouth FC 05/11/1949 | £35.00 |