| Brentford FC v Chelsea FC 20/08/1938 | View match | |
| Liverpool FC v Chelsea FC 27/08/1938 | View match | |
| Chelsea FC v Preston North End FC 31/08/1938 | View match | |
| Chelsea FC v Leicester City FC 03/09/1938 | View match | |
| Bolton Wanderers FC v Chelsea FC 05/09/1938 | View match | |
| Middlesbrough FC v Chelsea FC 10/09/1938 | View match | |
| Chelsea FC v Birmingham 17/09/1938 | View match | |
| Manchester United FC v Chelsea FC 24/09/1938 | View match | |
| Chelsea FC v Stoke City FC 01/10/1938 | View match | |
| Blackpool FC v Chelsea FC 08/10/1938 | View match | |
| Chelsea FC v Arsenal FC 15/10/1938 | View match | |
| Brentford FC v Chelsea FC 22/10/1938 | View match |