| 6. Jornada | 28.08.1999 | Aston Villa | - | Middlesbrough | 1:0 | ||||
| 7. Jornada | 11.09.1999 | Middlesbrough | - | Southampton | 3:2 | ||||
| 15. Jornada | 20.11.1999 | Arsenal | - | Middlesbrough | 5:1 | ||||
| 19. Jornada | 26.12.1999 | Sheffield Wednesday | - | Middlesbrough | 1:0 | ||||
| 23. Jornada | 22.01.2000 | Liverpool | - | Middlesbrough | 0:0 | ||||
| 21. Jornada | 29.01.2000 | Manchester United | - | Middlesbrough | 1:0 |
Irlanda