| 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 | |
| Bolton Wanderers FC v Portsmouth FC 04/02/1950 | View match | |
| Manchester United FC v Portsmouth FC 11/02/1950 | View match | |
| Portsmouth FC v Manchester United FC 15/02/1950 | View match |