| Liverpool FC v Portsmouth FC 03/12/1949 | View match | |
| Portsmouth FC v Arsenal FC 10/12/1949 | View match | |
| Portsmouth FC v Newcastle United FC 17/12/1949 | View match | |
| Blackpool FC v Portsmouth FC 24/12/1949 | View match | |
| Charlton Athletic FC v Portsmouth FC 26/12/1949 | £30.00 | |
| Portsmouth FC v Charlton Athletic FC 27/12/1949 | View match | |
| Portsmouth FC v Middlesbrough FC 31/12/1949 | View match | |
| Portsmouth FC v Norwich City FC 07/01/1950 | View match | |
| Norwich City FC v Portsmouth FC 12/01/1950 | View match | |
| Everton FC v Portsmouth FC 14/01/1950 | View match | |
| Portsmouth FC v Huddersfield Town FC 21/01/1950 | View match | |
| Portsmouth FC v Grimsby Town FC 28/01/1950 | View match |