| 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 | |
| Leeds United FC v Chelsea FC 19/04/1958 | View match | |
| Chelsea FC v Canto Do Rio 22/04/1958 | £12.50 | |
| Chelsea FC v Canto Do Rio 22/04/1958 | £9.99 | |
| Chelsea FC v Manchester United FC 26/04/1958 | View match | |
| Manchester United FC v Chelsea FC 23/08/1958 | £10.00 | |
| Chelsea FC v Tottenham Hotspur FC 27/08/1958 | £8.00 | |
| Chelsea FC v Wolverhampton Wanderers FC 30/08/1958 | £12.99 | |
| Chelsea FC v Wolverhampton Wanderers FC 30/08/1958 | £8.50 |