| Oldham Athletic FC v Portsmouth FC 01/09/1990 | View match | |
| Portsmouth FC v Port Vale FC 08/09/1990 | View match | |
| Notts County FC v Portsmouth FC 15/09/1990 | View match | |
| Brighton & Hove Albion FC v Portsmouth FC 19/09/1990 | £3.00 | |
| Portsmouth FC v Blackburn Rovers FC 22/09/1990 | View match | |
| Cardiff City FC v Portsmouth FC 25/09/1990 | View match | |
| Portsmouth FC v Plymouth Argyle FC 29/09/1990 | View match | |
| Millwall FC v Portsmouth FC 03/10/1990 | View match | |
| Newcastle United FC v Portsmouth FC 06/10/1990 | View match | |
| Portsmouth FC v Cardiff City FC 09/10/1990 | View match | |
| Portsmouth FC v Barnsley FC 13/10/1990 | View match | |
| Portsmouth FC v Leicester City FC 20/10/1990 | View match |