| Portsmouth FC v Leicester City FC 08/11/1958 | View match | |
| Preston North End FC v Portsmouth FC 15/11/1958 | View match | |
| Portsmouth FC v Burnley FC 22/11/1958 | View match | |
| Bolton Wanderers FC v Portsmouth FC 29/11/1958 | View match | |
| Portsmouth FC v Arsenal FC 06/12/1958 | View match | |
| Everton FC v Portsmouth FC 13/12/1958 | View match | |
| West Ham United FC v Portsmouth FC 20/12/1958 | View match | |
| Portsmouth FC v Wolverhampton Wanderers FC 26/12/1958 | View match | |
| Wolverhampton Wanderers FC v Portsmouth FC 27/12/1958 | £7.99 | |
| Portsmouth FC v Nottingham Forest FC 03/01/1959 | View match | |
| Portsmouth FC v Swansea Town 10/01/1959 | View match | |
| Chelsea FC v Portsmouth FC 17/01/1959 |