| Manchester City FC v Chelsea FC 04/09/1957 | View match | |
| Everton FC v Chelsea FC 07/09/1957 | View match | |
| Chelsea FC v West Bromwich Albion FC 11/09/1957 | £14.00 | |
| Chelsea FC v West Bromwich Albion FC 11/09/1957 | £9.99 | |
| Newcastle United FC v Chelsea FC 14/09/1957 | View match | |
| West Bromwich Albion FC v Chelsea FC 18/09/1957 | View match | |
| Chelsea FC v Burnley FC 21/09/1957 | £4.99 | |
| Preston North End FC v Chelsea FC 28/09/1957 | View match | |
| Chelsea FC v Sheffield Wednesday FC 05/10/1957 | View match | |
| Chelsea FC v Aston Villa FC 12/10/1957 | £18.99 | |
| Wolverhampton Wanderers FC v Chelsea FC 19/10/1957 | View match | |
| Chelsea FC v Arsenal FC 26/10/1957 | £10.00 |