| Chelsea FC v Leeds United FC 08/11/1958 | View match | |
| Manchester City FC v Chelsea FC 15/11/1958 | View match | |
| Chelsea FC v Arsenal FC 22/11/1958 | View match | |
| Everton FC v Chelsea FC 29/11/1958 | View match | |
| Chelsea FC v Birmingham City FC 06/12/1958 | View match | |
| West Bromwich Albion FC v Chelsea FC 13/12/1958 | View match | |
| 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 | |
| Wolverhampton Wanderers FC v Chelsea FC 03/01/1959 | View match | |
| Chelsea FC v Portsmouth FC 17/01/1959 | £3.00 | |
| Newcastle United FC v Chelsea FC 19/01/1959 | View match |