1. Jornada | 07.08.1999 | Middlesbrough | - | Bradford City | 0:1 | ||||
2. Jornada | 10.08.1999 | Wimbledon FC | - | Middlesbrough | 2:3 | ||||
4. Jornada | 21.08.1999 | Middlesbrough | - | Liverpool | 1:0 | ||||
7. Jornada | 11.09.1999 | Middlesbrough | - | Southampton | 3:2 | ||||
9. Jornada | 25.09.1999 | Middlesbrough | - | Chelsea | 0:1 | ||||
15. Jornada | 20.11.1999 | Arsenal | - | Middlesbrough | 5:1 | ||||
17. Jornada | 04.12.1999 | Bradford City | - | Middlesbrough | 1:1 | ||||
25. Jornada | 14.02.2000 | Middlesbrough | - | Aston Villa | 0:4 |