| 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 | |
| Leeds United FC v Chelsea FC 10/10/1955 | View match | |
| Chelsea FC v Tottenham Hotspur FC 15/10/1955 | £11.00 | |
| Brentford FC v Chelsea FC 18/10/1955 | £35.99 | |
| Preston North End FC v Chelsea FC 22/10/1955 | View match | |
| Chelsea FC v Burnley FC 29/10/1955 | £8.50 | |
| Chelsea FC v Burnley FC 29/10/1955 | £7.50 | |
| Birmingham City FC v Chelsea FC 05/11/1955 | View match | |
| Millwall FC v Chelsea FC 07/11/1955 | View match |