| Portsmouth FC v Clapton Orient 22/01/1944 | View match | |
| Reading FC v Portsmouth FC 29/01/1944 | View match | |
| Portsmouth FC v Crystal Palace FC 05/02/1944 | £75.00 | |
| Portsmouth FC v Charlton Athletic FC 12/02/1944 | View match | |
| Portsmouth FC v Aldershot F.C 19/02/1944 | £165.00 | |
| Portsmouth FC v Aldershot F.C 19/02/1944 | £145.00 | |
| Tottenham Hotspur FC v Portsmouth FC 26/02/1944 | View match | |
| Portsmouth FC v Brentford FC 04/03/1944 | View match | |
| Aldershot F.C v Portsmouth FC 11/03/1944 | View match | |
| Portsmouth FC v Tottenham Hotspur FC 18/03/1944 | View match | |
| Queens Park Rangers FC v Portsmouth FC 10/04/1944 | View match | |
| Brighton & Hove Albion FC v Portsmouth FC 22/04/1944 | View match |