| Newcastle United FC v Chelsea FC 17/04/1909 | View match | |
| Bradford City FC v Chelsea FC 20/04/1909 | View match | |
| Chelsea FC v Bristol City FC 26/04/1909 | View match | |
| Chelsea FC v Leicester Fosse 29/04/1909 | View match | |
| Chelsea FC v Notts County FC 01/09/1909 | View match | |
| Chelsea FC v Sheffield United FC 04/09/1909 | View match | |
| Chelsea FC v Liverpool FC 04/09/1909 | View match | |
| Aston Villa FC v Chelsea FC 11/09/1909 | View match | |
| Woolwich Arsenal v Chelsea FC 25/09/1909 | View match | |
| Chelsea FC v Bolton Wanderers FC 02/10/1909 | View match | |
| Middlesbrough FC v Chelsea FC 09/10/1909 | View match | |
| Blackburn Rovers FC v Chelsea FC 16/10/1909 | View match |