| 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 | |
| Chelsea FC v Birmingham City FC 15/09/1956 | £3.50 | |
| Chelsea FC v Sheffield Wednesday FC 19/09/1956 | View match | |
| West Bromwich Albion FC v Chelsea FC 22/09/1956 | View match | |
| Chelsea FC v Portsmouth FC 29/09/1956 | £14.99 | |
| Chelsea FC v Tottenham Hotspur FC 01/10/1956 | View match | |
| Chelsea FC v Tottenham Hotspur FC 06/10/1956 | £12.00 | |
| Everton FC v Chelsea FC 13/10/1956 | View match |