| 2. Ronde | 22.08.2000 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
| 6. Ronde | 17.09.2000 | Manchester City | - | Middlesbrough FC | 1:1 | ||||
| 10. Ronde | 21.10.2000 | Charlton Athletic | - | Middlesbrough FC | 1:0 | ||||
| 11. Ronde | 28.10.2000 | Ipswich Town | - | Middlesbrough FC | 2:1 | ||||
| 12. Ronde | 04.11.2000 | Middlesbrough FC | - | Arsenal FC | 0:1 | ||||
| 13. Ronde | 11.11.2000 | Manchester United | - | Middlesbrough FC | 2:1 | ||||
| 26. Ronde | 03.02.2001 | Middlesbrough FC | - | Manchester City | 1:1 |
Engeland