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