| Wimbledon v Middlesbrough FC 25/03/1989 | View match | |
| Middlesbrough FC v Everton FC 27/03/1989 | View match | |
| Charlton Athletic FC v Middlesbrough FC 01/04/1989 | £3.00 | |
| Charlton Athletic FC v Middlesbrough FC 01/04/1989 | £3.00 | |
| Middlesbrough FC v Southampton FC 08/04/1989 | View match | |
| West Ham United FC v Middlesbrough FC 11/04/1989 | View match | |
| Queens Park Rangers FC v Middlesbrough FC 15/04/1989 | £1.50 | |
| Middlesbrough FC v Nottingham Forest FC 22/04/1989 | View match | |
| Aston Villa FC v Middlesbrough FC 29/04/1989 | ||
| Middlesbrough FC v Arsenal FC 06/05/1989 | View match | |
| Sheffield Wednesday FC v Middlesbrough FC 13/05/1989 | £2.50 | |
| Middlesbrough FC v Wolverhampton Wanderers FC 19/08/1989 | View match |