| 1. Jornada | 15.08.1998 | Middlesbrough | - | Leeds United | 0:0 | ||||
| 2. Jornada | 23.08.1998 | Aston Villa | - | Middlesbrough | 3:1 | ||||
| 3. Jornada | 29.08.1998 | Middlesbrough | - | Derby County | 1:1 | ||||
| 7. Jornada | 26.09.1998 | Chelsea | - | Middlesbrough | 2:0 | ||||
| 9. Jornada | 17.10.1998 | Middlesbrough | - | Blackburn Rovers | 2:1 | ||||
| 10. Jornada | 24.10.1998 | Wimbledon FC | - | Middlesbrough | 2:2 | ||||
| 11. Jornada | 01.11.1998 | Middlesbrough | - | Nottingham Forest | 1:1 | ||||
| 12. Jornada | 07.11.1998 | Southampton | - | Middlesbrough | 3:3 |  |
|||
| 13. Jornada | 14.11.1998 | Charlton Athletic | - | Middlesbrough | 1:1 |  |
|||
| 16. Jornada | 06.12.1998 | Middlesbrough | - | Newcastle United | 2:2 | ||||
| 17. Jornada | 12.12.1998 | Middlesbrough | - | West Ham United | 1:0 | ||||
| 19. Jornada | 26.12.1998 | Middlesbrough | - | Liverpool | 1:3 | ||||
| 20. Jornada | 28.12.1998 | Derby County | - | Middlesbrough | 2:1 | ||||
| 23. Jornada | 30.01.1999 | Middlesbrough | - | Leicester City | 0:0 |  |
|||
| 24. Jornada | 06.02.1999 | Liverpool | - | Middlesbrough | 3:1 | |
|||
| 29. Jornada | 14.03.1999 | Middlesbrough | - | Southampton | 3:0 |
Inglaterra