1. Round | 19/08/2000 | Coventry City | - | Middlesbrough FC | 1:3 | ||||
2. Round | 22/08/2000 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
3. Round | 26/08/2000 | Middlesbrough FC | - | Leeds United | 1:2 | ||||
4. Round | 06/09/2000 | Derby County | - | Middlesbrough FC | 3:3 | ||||
9. Round | 16/10/2000 | Middlesbrough FC | - | Newcastle United | 1:3 | ||||
10. Round | 21/10/2000 | Charlton Athletic | - | Middlesbrough FC | 1:0 | ||||
12. Round | 04/11/2000 | Middlesbrough FC | - | Arsenal FC | 0:1 | ||||
13. Round | 11/11/2000 | Manchester United | - | Middlesbrough FC | 2:1 |