| Chelsea FC v Bolton Wanderers FC 20/08/1955 | View match | |
| Huddersfield Town FC v Chelsea FC 24/08/1955 | View match | |
| Arsenal FC v Chelsea FC 27/08/1955 | View match | |
| Chelsea FC v Huddersfield Town FC 29/08/1955 | View match | |
| Chelsea FC v Portsmouth FC 03/09/1955 | View match | |
| Blackpool FC v Chelsea FC 05/09/1955 | View match | |
| Sunderland FC v Chelsea FC 10/09/1955 | View match | |
| Chelsea FC v Newcastle United FC 14/09/1955 | View match | |
| Chelsea FC v Aston Villa FC 17/09/1955 | View match | |
| Wolverhampton Wanderers FC v Chelsea FC 24/09/1955 | View match | |
| Chelsea FC v Manchester City FC 01/10/1955 | View match | |
| Charlton Athletic FC v Chelsea FC 08/10/1955 | £12.99 |