| 2. Ronde | 22.08.2000 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 |  |
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| 4. Ronde | 06.09.2000 | Derby County | - | Middlesbrough FC | 3:3 | |
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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 | ||||
| 11. Ronde | 28.10.2000 | Ipswich Town | - | Middlesbrough FC | 2:1 | |
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| 12. Ronde | 04.11.2000 | Middlesbrough FC | - | Arsenal FC | 0:1 | |
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| 13. Ronde | 11.11.2000 | Manchester United | - | Middlesbrough FC | 2:1 |
Engeland