| Chelsea FC v Bolton Wanderers FC 06/05/1939 | View match | |
| Chelsea FC v Bolton Wanderers FC 27/08/1939 | View match | |
| Chelsea FC v Manchester United FC 30/08/1939 | View match | |
| Liverpool FC v Chelsea FC 02/09/1939 | View match | |
| Chelsea FC v Arsenal FC 07/10/1939 | View match | |
| Chelmsford City v Chelsea FC 18/11/1939 | View match | |
| Chelsea FC v Fulham FC 22/03/1940 | View match | |
| Chelsea FC v West Ham United FC 27/04/1940 | View match | |
| Crystal Palace FC v Chelsea FC 31/08/1940 | View match | |
| Chelsea FC v Brentford FC 07/09/1940 | View match | |
| Tottenham Hotspur FC v Chelsea FC 14/09/1940 | View match | |
| Chelsea FC v Tottenham Hotspur FC 21/09/1940 | View match |