| Chelsea FC v Watford FC 22/04/1944 | View match | |
| Chelsea FC v Reading FC 29/04/1944 | View match | |
| Millwall FC v Chelsea FC 06/05/1944 | View match | |
| Fulham FC v Chelsea FC 26/08/1944 | View match | |
| Chelsea FC v Aldershot F.C 02/09/1944 | View match | |
| Brentford FC v Chelsea FC 09/09/1944 | View match | |
| Chelsea FC v Crystal Palace FC 16/09/1944 | View match | |
| Charlton Athletic FC v Chelsea FC 23/09/1944 | View match | |
| Chelsea FC v Clapton Orient 30/09/1944 | View match | |
| Portsmouth FC v Chelsea FC 07/10/1944 | View match | |
| Aldershot F.C v Chelsea FC 11/10/1944 | View match | |
| Tottenham Hotspur FC v Chelsea FC 14/10/1944 | View match |