| Portsmouth FC v Birmingham City FC 15/03/1969 | View match | |
| Cardiff City FC v Portsmouth FC 21/03/1969 | View match | |
| Portsmouth FC v Newport County 24/03/1969 | View match | |
| Portsmouth FC v Newport County XI 24/03/1969 | View match | |
| Portsmouth FC v Charlton Athletic FC 29/03/1969 | £4.50 | |
| Crystal Palace FC v Portsmouth FC 05/04/1969 | View match | |
| Blackburn Rovers FC v Portsmouth FC 07/04/1969 | View match | |
| Portsmouth FC v Carlisle United FC 09/04/1969 | View match | |
| Portsmouth FC v Norwich City FC 12/04/1969 | View match | |
| Bury FC v Portsmouth FC 18/04/1969 | View match | |
| Bristol Rovers FC v Portsmouth FC 26/07/1969 | View match | |
| Blackpool FC v Portsmouth FC 09/08/1969 | View match |