| Chelsea FC v Liverpool FC 11/10/1919 | View match | |
| Liverpool FC v Chelsea FC 18/10/1919 | View match | |
| Bradford Park Avenue v Chelsea FC 25/10/1919 | View match | |
| Chelsea FC v Bradford Park Avenue 01/11/1919 | View match | |
| Preston North End FC v Chelsea FC 08/11/1919 | View match | |
| Chelsea FC v Preston North End FC 15/11/1919 | View match | |
| Middlesbrough FC v Chelsea FC 22/11/1919 | View match | |
| Chelsea FC v Middlesbrough FC 29/11/1919 | View match | |
| Arsenal FC v Chelsea FC 06/12/1919 | View match | |
| Chelsea FC v Arsenal FC 13/12/1919 | View match | |
| Sheffield United FC v Chelsea FC 20/12/1919 | View match | |
| Aston Villa FC v Chelsea FC 25/12/1919 | View match |