| 1. Ronde | 19.08.2000 | Coventry City | - | Middlesbrough FC | 1:3 |  |
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| 2. Ronde | 22.08.2000 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
| 3. Ronde | 26.08.2000 | Middlesbrough FC | - | Leeds United | 1:2 | ||||
| 4. Ronde | 06.09.2000 | Derby County | - | Middlesbrough FC | 3:3 | |
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| 5. Ronde | 09.09.2000 | Middlesbrough FC | - | Everton FC | 1:2 | ||||
| 6. Ronde | 17.09.2000 | Manchester City | - | Middlesbrough FC | 1:1 | ||||
| 7. Ronde | 23.09.2000 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
| 11. Ronde | 28.10.2000 | Ipswich Town | - | Middlesbrough FC | 2:1 | ||||
| 14. Ronde | 18.11.2000 | Middlesbrough FC | - | Leicester City | 0:3 | ||||
| 15. Ronde | 25.11.2000 | Middlesbrough FC | - | Bradford City | 2:2 | ||||
| 16. Ronde | 02.12.2000 | West Ham United | - | Middlesbrough FC | 1:0 | ||||
| 38. Ronde | 19.05.2001 | Middlesbrough FC | - | West Ham United | 2:1 | |
Frankrijk