| Bournemouth & Boscombe v Portsmouth FC 21/03/1959 | View match | |
| Manchester United FC v Portsmouth FC 27/03/1959 | £13.99 | |
| Leicester City FC v Portsmouth FC 28/03/1959 | View match | |
| Portsmouth FC v Manchester United FC 30/03/1959 | View match | |
| Portsmouth FC v Preston North End FC 04/04/1959 | View match | |
| Burnley FC v Portsmouth FC 11/04/1959 | View match | |
| Portsmouth FC v Everton FC 15/04/1959 | View match | |
| Portsmouth FC v Bolton Wanderers FC 18/04/1959 | View match | |
| Luton Town FC v Portsmouth FC 22/04/1959 | View match | |
| Arsenal FC v Portsmouth FC 25/04/1959 | View match | |
| Southend United FC v Portsmouth FC 27/04/1959 | View match | |
| Middlesbrough FC v Portsmouth FC 22/08/1959 | View match |