| Portsmouth FC v Brentford FC 29/04/1944 | View match | |
| Luton Town FC v Portsmouth FC 06/05/1944 | View match | |
| Portsmouth FC v Clapton Orient 26/08/1944 | £85.00 | |
| Portsmouth FC v Brentford FC 02/09/1944 | £65.00 | |
| Portsmouth FC v Charlton Athletic FC 09/09/1944 | £70.00 | |
| Tottenham Hotspur FC v Portsmouth FC 16/09/1944 | View match | |
| Portsmouth FC v West Ham United FC 23/09/1944 | £45.00 | |
| Portsmouth FC v Southampton FC 30/09/1944 | £65.00 | |
| Portsmouth FC v Chelsea FC 07/10/1944 | £65.00 | |
| Millwall FC v Portsmouth FC 14/10/1944 | View match | |
| Watford FC v Portsmouth FC 21/10/1944 | View match | |
| Portsmouth FC v Aldershot F.C 28/10/1944 | £70.00 |