| Chelsea FC v Portsmouth FC 25/12/1957 | View match | |
| Portsmouth FC v Chelsea FC 26/12/1957 | View match | |
| Birmingham City FC v Chelsea FC 28/12/1957 | View match | |
| Doncaster Rovers FC v Chelsea FC 04/01/1958 | View match | |
| Chelsea FC v Everton FC 11/01/1958 | View match | |
| Chelsea FC v Newcastle United FC 18/01/1958 | £11.00 | |
| Chelsea FC v Darlington FC 25/01/1958 | £18.00 | |
| Darlington FC v Chelsea FC 29/01/1958 | View match | |
| Burnley FC v Chelsea FC 01/02/1958 | View match | |
| Chelsea FC v Preston North End FC 08/02/1958 | £4.50 | |
| Chelsea FC v Preston North End FC 08/02/1958 | £11.00 | |
| Chelsea FC v Preston North End FC 08/02/1958 | £10.00 |