| 5. Round | 15/09/2001 | Middlesbrough FC | - | West Ham United | 2:0 | ||||
| 7. Round | 23/09/2001 | Chelsea FC | - | Middlesbrough FC | 2:2 |  |
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| 9. Round | 13/10/2001 | Charlton Athletic | - | Middlesbrough FC | 0:0 | ||||
| 15. Round | 01/12/2001 | Blackburn Rovers | - | Middlesbrough FC | 0:1 | ||||
| 21. Round | 01/01/2002 | Middlesbrough FC | - | Everton FC | 1:0 | |
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| 24. Round | 29/01/2002 | Sunderland AFC | - | Middlesbrough FC | 0:1 | ||||
| 25. Round | 03/02/2002 | Middlesbrough FC | - | Charlton Athletic | 0:0 | ||||
| 26. Round | 09/02/2002 | Middlesbrough FC | - | Leeds United | 2:2 | ||||
| 30. Round | 16/03/2002 | Middlesbrough FC | - | Liverpool FC | 1:2 |
Ireland