| Everton FC v Leicester City FC 20/12/1958 | View match | |
| Everton FC v Bolton Wanderers FC 26/12/1958 | View match | |
| Bolton Wanderers FC v Everton FC 27/12/1958 | View match | |
| Newcastle United FC v Everton FC 03/01/1959 | View match | |
| Everton FC v Sunderland FC 10/01/1959 | View match | |
| Arsenal FC v Everton FC 17/01/1959 | £5.50 | |
| Charlton Athletic FC v Everton FC 24/01/1959 | £7.00 | |
| Everton FC v Charlton Athletic FC 28/01/1959 | View match | |
| Everton FC v Manchester City FC 31/01/1959 | View match | |
| Leeds United FC v Everton FC 07/02/1959 | View match | |
| Everton FC v Aston Villa FC 14/02/1959 | View match | |
| Everton FC v West Bromwich Albion FC 18/02/1959 | View match |