| Charlton Athletic FC v Portsmouth FC 04/10/1969 | £4.50 | |
| Sheffield United FC v Portsmouth FC 07/10/1969 | View match | |
| Portsmouth FC v Bristol City FC 11/10/1969 | View match | |
| Watford FC v Portsmouth FC 18/10/1969 | View match | |
| Portsmouth FC v Swindon Town FC 25/10/1969 | View match | |
| Carlisle United FC v Portsmouth FC 01/11/1969 | View match | |
| Portsmouth FC v Cardiff City FC 08/11/1969 | View match | |
| Portsmouth FC v Birmingham City FC 12/11/1969 | View match | |
| Huddersfield Town FC v Portsmouth FC 15/11/1969 | View match | |
| Portsmouth FC v Middlesbrough FC 22/11/1969 | View match | |
| Portsmouth FC v Preston North End FC 06/12/1969 | View match | |
| Millwall FC v Portsmouth FC 08/12/1969 | View match |