| 26. Round | 09/02/2002 | Middlesbrough FC | - | Leeds United | 2:2 | ||||
| 18. Round | 19/02/2002 | Middlesbrough FC | - | Fulham FC | 2:1 | ||||
| 27. Round | 23/02/2002 | West Ham United | - | Middlesbrough FC | 1:0 | ||||
| 28. Round | 02/03/2002 | Middlesbrough FC | - | Leicester City | 1:0 |  |
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| 29. Round | 06/03/2002 | Southampton FC | - | Middlesbrough FC | 1:1 | ||||
| 30. Round | 16/03/2002 | Middlesbrough FC | - | Liverpool FC | 1:2 | ||||
| 31. Round | 23/03/2002 | Manchester United | - | Middlesbrough FC | 0:1 | ||||
| 32. Round | 30/03/2002 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
| 33. Round | 01/04/2002 | Derby County | - | Middlesbrough FC | 0:1 | ||||
| 34. Round | 06/04/2002 | Middlesbrough FC | - | Aston Villa | 2:1 |  |
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| 36. Round | 20/04/2002 | Middlesbrough FC | - | Blackburn Rovers | 1:3 | ||||
| 35. Round | 24/04/2002 | Ipswich Town | - | Middlesbrough FC | 1:0 | ||||
| 37. Round | 27/04/2002 | Middlesbrough FC | - | Chelsea FC | 0:2 |
Italy