| Chelsea FC v Aston Villa FC 13/09/1958 | View match | |
| Newcastle United FC v Chelsea FC 17/09/1958 | View match | |
| West Ham United FC v Chelsea FC 20/09/1958 | View match | |
| Chelsea FC v Nottingham Forest FC 27/09/1958 | £4.50 | |
| Frem (Copenhagen) v Chelsea FC 30/09/1958 | View match | |
| Burnley FC v Chelsea FC 04/10/1958 | View match | |
| Chelsea FC v Bolton Wanderers FC 11/10/1958 | View match | |
| Luton Town FC v Chelsea FC 18/10/1958 | View match | |
| Chelsea FC v Leicester City FC 25/10/1958 | View match | |
| Chelsea FC v South Africans 28/10/1958 | View match | |
| Preston North End FC v Chelsea FC 01/11/1958 | View match | |
| Chelsea FC v Frem (Copenhagen) 04/11/1958 | View match |