| Chelsea FC v Luton Town FC 02/04/1956 | View match | |
| Sheffield United FC v Chelsea FC 07/04/1956 | View match | |
| Chelsea FC v Everton FC 14/04/1956 | £11.00 | |
| Newcastle United FC v Chelsea FC 21/04/1956 | View match | |
| Chelsea FC v Blackpool FC 28/04/1956 | View match | |
| Southend United FC v Chelsea FC 30/04/1956 | View match | |
| Burnley FC v Chelsea FC 18/08/1956 | View match | |
| Sheffield Wednesday FC v Chelsea FC 22/08/1956 | View match | |
| Chelsea FC v Preston North End FC 25/08/1956 | View match | |
| Leeds United FC v Chelsea FC 01/09/1956 | View match | |
| Chelsea FC v Manchester United FC 05/09/1956 | View match | |
| Cardiff City FC v Chelsea FC 08/09/1956 | View match |