| Chelsea FC v Canto Do Rio 22/04/1958 | £9.99 | |
| 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 | |
| Tottenham Hotspur FC v Chelsea FC 03/09/1958 | £18.99 | |
| Chelsea FC v Newcastle United FC 10/09/1958 | £8.00 | |
| Chelsea FC v Newcastle United FC 10/09/1958 | £5.50 | |
| Chelsea FC v Nottingham Forest FC 27/09/1958 | £4.50 | |
| Chelsea FC v Manchester United FC 20/12/1958 | £10.99 | |
| Blackburn Rovers FC v Chelsea FC 25/12/1958 | £4.50 | |
| Chelsea FC v Blackburn Rovers FC 27/12/1958 | £2.50 |