| Middlesbrough FC v Aston Villa FC 10/12/1988 | View match | |
| Middlesbrough FC v Oldham Athletic FC 14/12/1988 | View match | |
| Middlesbrough FC v Charlton Athletic FC 17/12/1988 | £4.50 | |
| Middlesbrough FC v Portsmouth FC 21/12/1988 | View match | |
| Everton FC v Middlesbrough FC 26/12/1988 | View match | |
| Norwich City FC v Middlesbrough FC 31/12/1988 | View match | |
| 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 |