| Chelsea FC v Charlton Athletic FC 29/08/1953 | View match | |
| Portsmouth FC v Chelsea FC 02/09/1953 | View match | |
| Chelsea FC v Sheffield United FC 05/09/1953 | £11.50 | |
| Arsenal FC v Chelsea FC 08/09/1953 | View match | |
| Huddersfield Town FC v Chelsea FC 12/09/1953 | View match | |
| Chelsea FC v Arsenal FC 15/09/1953 | £14.00 | |
| Chelsea FC v Aston Villa FC 19/09/1953 | £10.00 | |
| Wolverhampton Wanderers FC v Chelsea FC 26/09/1953 | View match | |
| Chelsea FC v Sunderland FC 03/10/1953 | £12.00 | |
| Sheffield Wednesday FC v Chelsea FC 10/10/1953 | View match | |
| Chelsea FC v Middlesbrough FC 17/10/1953 | View match | |
| West Bromwich Albion FC v Chelsea FC 24/10/1953 | View match |