2. Round | 22/08/2000 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
4. Round | 06/09/2000 | Derby County | - | Middlesbrough FC | 3:3 | ||||
7. Round | 23/09/2000 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
8. Round | 30/09/2000 | Southampton FC | - | Middlesbrough FC | 1:3 | ||||
11. Round | 28/10/2000 | Ipswich Town | - | Middlesbrough FC | 2:1 | ||||
12. Round | 04/11/2000 | Middlesbrough FC | - | Arsenal FC | 0:1 | ||||
13. Round | 11/11/2000 | Manchester United | - | Middlesbrough FC | 2:1 |