| Accrington Stanley (1891) v Portsmouth FC 24/01/1959 | View match | |
| Portsmouth FC v Accrington Stanley (1891) 28/01/1959 | View match | |
| Portsmouth FC v Blackpool FC 31/01/1959 | View match | |
| Blackburn Rovers FC v Portsmouth FC 07/02/1959 | View match | |
| Burnley FC v Portsmouth FC 14/02/1959 | £11.50 | |
| Tottenham Hotspur FC v Portsmouth FC 21/02/1959 | View match | |
| Leeds United FC v Portsmouth FC 28/02/1959 | View match | |
| Portsmouth FC v Manchester City FC 07/03/1959 | View match | |
| Portsmouth FC v Newcastle United FC 11/03/1959 | View match | |
| Portsmouth FC v Birmingham City FC 21/03/1959 | View match | |
| Bournemouth & Boscombe v Portsmouth FC 21/03/1959 | View match | |
| Manchester United FC v Portsmouth FC 27/03/1959 | £13.99 |