| Portsmouth FC v Bristol City FC 28/12/1968 | View match | |
| Portsmouth FC v Chesterfield FC 04/01/1969 | View match | |
| Sheffield United FC v Portsmouth FC 11/01/1969 | View match | |
| Portsmouth FC v Fulham FC 18/01/1969 | View match | |
| Blackburn Rovers FC v Portsmouth FC 25/01/1969 | View match | |
| Aston Villa FC v Portsmouth FC 01/02/1969 | View match | |
| Portsmouth FC v Hull City FC 08/02/1969 | £3.00 | |
| Millwall FC v Portsmouth FC 15/02/1969 | View match | |
| Portsmouth FC v Bolton Wanderers FC 22/02/1969 | View match | |
| Portsmouth FC v Huddersfield Town FC 01/03/1969 | View match | |
| Oxford United FC v Portsmouth FC 05/03/1969 | View match | |
| Middlesbrough FC v Portsmouth FC 08/03/1969 | View match |