| 7. Ronde | 23.09.2000 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
| 9. Ronde | 16.10.2000 | Middlesbrough FC | - | Newcastle United | 1:3 | ||||
| 10. Ronde | 21.10.2000 | Charlton Athletic | - | Middlesbrough FC | 1:0 | ||||
| 11. Ronde | 28.10.2000 | Ipswich Town | - | Middlesbrough FC | 2:1 | ||||
| 13. Ronde | 11.11.2000 | Manchester United | - | Middlesbrough FC | 2:1 | ||||
| 14. Ronde | 18.11.2000 | Middlesbrough FC | - | Leicester City | 0:3 |  |
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| 15. Ronde | 25.11.2000 | Middlesbrough FC | - | Bradford City | 2:2 |  |
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| 28. Ronde | 24.02.2001 | Middlesbrough FC | - | Southampton FC | 0:1 | ||||
| 31. Ronde | 31.03.2001 | Chelsea FC | - | Middlesbrough FC | 2:1 | ||||
| 34. Ronde | 16.04.2001 | Middlesbrough FC | - | Ipswich Town | 1:2 | ||||
| 36. Ronde | 28.04.2001 | Middlesbrough FC | - | Manchester United | 0:2 | ||||
| 37. Ronde | 05.05.2001 | Bradford City | - | Middlesbrough FC | 1:1 | ||||
| 38. Ronde | 19.05.2001 | Middlesbrough FC | - | West Ham United | 2:1 |
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