| 1. Ronde | 19.08.2000 | Coventry City | - | Middlesbrough FC | 1:3 | ||||
| 2. Ronde | 22.08.2000 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
| 3. Ronde | 26.08.2000 | Middlesbrough FC | - | Leeds United | 1:2 | ||||
| 6. Ronde | 17.09.2000 | Manchester City | - | Middlesbrough FC | 1:1 |  |
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| 7. Ronde | 23.09.2000 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
| 8. Ronde | 30.09.2000 | Southampton FC | - | Middlesbrough FC | 1:3 | |
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| 17. Ronde | 09.12.2000 | Sunderland AFC | - | Middlesbrough FC | 1:0 | |
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| 18. Ronde | 16.12.2000 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
| 19. Ronde | 23.12.2000 | Tottenham Hotspur | - | Middlesbrough FC | 0:0 | |
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| 20. Ronde | 26.12.2000 | Middlesbrough FC | - | Liverpool FC | 1:0 | ||||
| 21. Ronde | 30.12.2000 | Middlesbrough FC | - | Coventry City | 1:1 | ||||
| 23. Ronde | 13.01.2001 | Middlesbrough FC | - | Derby County | 4:0 | ||||
| 26. Ronde | 03.02.2001 | Middlesbrough FC | - | Manchester City | 1:1 |  |
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| 27. Ronde | 10.02.2001 | Aston Villa | - | Middlesbrough FC | 1:1 | ||||
| 31. Ronde | 31.03.2001 | Chelsea FC | - | Middlesbrough FC | 2:1 |
Ierland