| 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 | |
| Chelsea FC v Portsmouth FC 17/01/1959 | £3.00 | |
| Chelsea FC v Aston Villa FC 24/01/1959 | £3.50 | |
| Chelsea FC v Aston Villa FC 24/01/1959 | £7.50 | |
| Chelsea FC v West Ham United FC 07/02/1959 | £12.99 | |
| Chelsea FC v West Bromwich Albion FC 22/04/1959 | £3.50 | |
| Chelsea FC v Ville De Belgrade 29/04/1959 | £28.99 | |
| Chelsea FC v Preston North End FC 22/08/1959 | £8.50 |