8. Round | 30/09/2000 | Southampton FC | - | Middlesbrough FC | 1:3 | ||||
9. Round | 16/10/2000 | Middlesbrough FC | - | Newcastle United | 1:3 | ||||
10. Round | 21/10/2000 | Charlton Athletic | - | Middlesbrough FC | 1:0 | ||||
11. Round | 28/10/2000 | Ipswich Town | - | Middlesbrough FC | 2:1 | ||||
12. Round | 04/11/2000 | Middlesbrough FC | - | Arsenal FC | 0:1 |