| Charlton Athletic FC v Middlesbrough FC 14/11/1998 | £4.00 | |
| Middlesbrough FC v Coventry City FC 21/11/1998 | View match | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Middlesbrough FC v Newcastle United FC 06/12/1998 | View match | |
| Middlesbrough FC v West Ham United FC 12/12/1998 | View match | |
| Manchester United FC v Middlesbrough FC 19/12/1998 | £4.50 | |
| Manchester United FC v Middlesbrough FC 19/12/1998 | £6.00 | |
| Middlesbrough FC v Liverpool FC 26/12/1998 | View match | |
| Derby County FC v Middlesbrough FC 28/12/1998 | View match |