| 1. Jornada | 07.08.1999 | Middlesbrough | - | Bradford City | 0:1 | ||||
| 2. Jornada | 10.08.1999 | Wimbledon FC | - | Middlesbrough | 2:3 |  |
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| 3. Jornada | 14.08.1999 | Derby County | - | Middlesbrough | 1:3 | ||||
| 4. Jornada | 21.08.1999 | Middlesbrough | - | Liverpool | 1:0 | |
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| 6. Jornada | 28.08.1999 | Aston Villa | - | Middlesbrough | 1:0 | ||||
| 7. Jornada | 11.09.1999 | Middlesbrough | - | Southampton | 3:2 | ||||
| 12. Jornada | 24.10.1999 | Watford FC | - | Middlesbrough | 1:3 | ||||
| 13. Jornada | 30.10.1999 | Middlesbrough | - | Everton | 2:1 | ||||
| 14. Jornada | 06.11.1999 | Middlesbrough | - | Sunderland | 1:1 | ||||
| 16. Jornada | 27.11.1999 | Middlesbrough | - | Wimbledon FC | 0:0 | ||||
| 17. Jornada | 04.12.1999 | Bradford City | - | Middlesbrough | 1:1 | |
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| 19. Jornada | 26.12.1999 | Sheffield Wednesday | - | Middlesbrough | 1:0 | |
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| 25. Jornada | 14.02.2000 | Middlesbrough | - | Aston Villa | 0:4 | ||||
| 33. Jornada | 15.04.2000 | Coventry City | - | Middlesbrough | 2:1 | ||||
| 36. Jornada | 29.04.2000 | West Ham United | - | Middlesbrough | 0:1 | |
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| 38. Jornada | 14.05.2000 | Everton | - | Middlesbrough | 0:2 | |
Inglaterra