| Scunthorpe United FC v Scarborough FC 29/08/1989 | View match | |
| Scarborough FC v Cambridge United FC 02/09/1989 | View match | |
| Scunthorpe United FC v Scarborough FC 09/09/1989 | View match | |
| Scarborough FC v Doncaster Rovers FC 16/09/1989 | View match | |
| Chelsea FC v Scarborough FC 19/09/1989 | £3.00 | |
| Colchester United FC v Scarborough FC 23/09/1989 | View match | |
| Scarborough FC v Halifax Town A.F.C 27/09/1989 | View match | |
| Stockport County FC v Scarborough FC 30/09/1989 | View match | |
| Scarborough FC v Chelsea FC 04/10/1989 | £9.50 | |
| Southend United FC v Scarborough FC 07/10/1989 | View match | |
| Scarborough FC v Grimsby Town FC 14/10/1989 | View match | |
| Hereford United v Scarborough FC 18/10/1989 | View match |