| Oldham Athletic FC v Plymouth Argyle FC 09/09/1989 | View match | |
| Portsmouth FC v Plymouth Argyle FC 12/09/1989 | View match | |
| Plymouth Argyle FC v Sheffield United FC 16/09/1989 | View match | |
| Arsenal FC v Plymouth Argyle FC 19/09/1989 | £4.50 | |
| Wolverhampton Wanderers FC v Plymouth Argyle FC 23/09/1989 | View match | |
| Swindon Town FC v Plymouth Argyle FC 26/09/1989 | View match | |
| Plymouth Argyle FC v Brighton & Hove Albion FC 30/09/1989 | £4.50 | |
| Plymouth Argyle FC v Arsenal FC 03/10/1989 | £6.00 | |
| Plymouth Argyle FC v Stoke City FC 07/10/1989 | View match | |
| Middlesbrough FC v Plymouth Argyle FC 14/10/1989 | View match | |
| Plymouth Argyle FC v Leicester City FC 17/10/1989 | View match | |
| Ipswich Town FC v Plymouth Argyle FC 21/10/1989 | View match |