| Birmingham City FC v Portsmouth FC 08/10/1949 | View match | |
| Portsmouth FC v Derby County FC 15/10/1949 | View match | |
| Portsmouth FC v Wolverhampton Wanderers FC 19/10/1949 | View match | |
| West Bromwich Albion FC v Portsmouth FC 22/10/1949 | View match | |
| Portsmouth FC v Manchester United FC 29/10/1949 | View match | |
| Chelsea FC v Portsmouth FC 05/11/1949 | £35.00 | |
| Portsmouth FC v Stoke City FC 12/11/1949 | View match | |
| Burnley FC v Portsmouth FC 19/11/1949 | View match | |
| Portsmouth FC v Sunderland FC 26/11/1949 | View match | |
| 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 |