| Middlesbrough FC v Manchester United FC 02/01/1989 | £4.00 | |
| Middlesbrough FC v Grimsby Town FC 07/01/1989 | View match | |
| Middlesbrough FC v Coventry City FC 11/01/1989 | View match | |
| Southampton FC v Middlesbrough FC 14/01/1989 | View match | |
| Middlesbrough FC v Tottenham Hotspur FC 21/01/1989 | View match | |
| Middlesbrough FC v Crystal Palace FC 28/01/1989 | View match | |
| Middlesbrough FC v Coventry City FC 04/02/1989 | View match | |
| Luton Town FC v Middlesbrough FC 18/02/1989 | £4.00 | |
| Millwall FC v Middlesbrough FC 21/02/1989 | View match | |
| Middlesbrough FC v Newcastle United FC 26/02/1989 | View match | |
| Middlesbrough FC v Liverpool FC 11/03/1989 | View match | |
| Middlesbrough FC v Derby County FC 18/03/1989 | View match |