| Chelsea FC v Sheffield United FC 23/01/1909 | View match | |
| Aston Villa FC v Chelsea FC 30/01/1909 | View match | |
| Blackburn Rovers FC v Chelsea FC 06/02/1909 | View match | |
| Sunderland FC v Chelsea FC 13/02/1909 | View match | |
| Chelsea FC v Blackburn Rovers FC 27/02/1909 | View match | |
| Chelsea FC v Manchester United FC 13/03/1909 | View match | |
| Everton FC v Chelsea FC 20/03/1909 | View match | |
| The Wednesday v Chelsea FC 22/03/1909 | View match | |
| Bury FC v Chelsea FC 31/03/1909 | View match | |
| Woolwich Arsenal v Chelsea FC 03/04/1909 | View match | |
| Chelsea FC v Middlesbrough FC 09/04/1909 | View match | |
| Chelsea FC v Notts County FC 10/04/1909 | View match |