| Sheffield Wednesday FC v Chelsea FC 15/02/1958 | View match | |
| Aston Villa FC v Chelsea FC 22/02/1958 | View match | |
| Arsenal FC v Chelsea FC 08/03/1958 | £6.00 | |
| Chelsea FC v Wolverhampton Wanderers FC 11/03/1958 | £14.99 | |
| Chelsea FC v Blackpool FC 15/03/1958 | £7.50 | |
| Leicester City FC v Chelsea FC 22/03/1958 | View match | |
| Chelsea FC v C.D.N.A Bulgaria 25/03/1958 | £12.00 | |
| Chelsea FC v Sunderland FC 29/03/1958 | View match | |
| Chelsea FC v Nottingham Forest FC 04/04/1958 | £5.00 | |
| Luton Town FC v Chelsea FC 05/04/1958 | View match | |
| Nottingham Forest FC v Chelsea FC 07/04/1958 | View match | |
| Chelsea FC v Bolton Wanderers FC 12/04/1958 | View match |