| Scunthorpe United FC v Liverpool FC 13/12/1958 | View match | |
| Grimsby Town FC v Liverpool FC 20/12/1958 | View match | |
| Rotherham United FC v Liverpool FC 26/12/1958 | View match | |
| Liverpool FC v Rotherham United FC 27/12/1958 | View match | |
| Liverpool FC v Sunderland FC 03/01/1959 | View match | |
| Worcester City v Liverpool FC 15/01/1959 | £169.99 | |
| Liverpool FC v Newcastle United FC 21/01/1959 | View match | |
| Charlton Athletic FC v Liverpool FC 31/01/1959 | View match | |
| Liverpool FC v Bristol City FC 07/02/1959 | View match | |
| Cardiff City FC v Liverpool FC 14/02/1959 | View match | |
| Liverpool FC v Huddersfield Town FC 21/02/1959 | View match | |
| Leyton Orient FC v Liverpool FC 28/02/1959 | View match |