| 1. Round | 18/08/2001 | Middlesbrough FC | - | Arsenal FC | 0:4 | ||||
| 5. Round | 15/09/2001 | Middlesbrough FC | - | West Ham United | 2:0 | ||||
| 6. Round | 17/09/2001 | Leicester City | - | Middlesbrough FC | 1:2 | ||||
| 7. Round | 23/09/2001 | Chelsea FC | - | Middlesbrough FC | 2:2 | ||||
| 8. Round | 29/09/2001 | Middlesbrough FC | - | Southampton FC | 1:3 | ||||
| 9. Round | 13/10/2001 | Charlton Athletic | - | Middlesbrough FC | 0:0 |  |
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| 10. Round | 22/10/2001 | Middlesbrough FC | - | Sunderland AFC | 2:0 | ||||
| 14. Round | 25/11/2001 | Middlesbrough FC | - | Ipswich Town | 0:0 | ||||
| 15. Round | 01/12/2001 | Blackburn Rovers | - | Middlesbrough FC | 0:1 | ||||
| 16. Round | 08/12/2001 | Liverpool FC | - | Middlesbrough FC | 2:0 |
England