| 23. Round | 18/01/1997 | Middlesbrough FC | - | Sheffield Wednesday | 4:2 |  |
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| 25. Round | 01/02/1997 | Wimbledon FC | - | Middlesbrough FC | 1:1 |  |
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| 28. Round | 22/02/1997 | Middlesbrough FC | - | Newcastle United | 0:1 | ||||
| 29. Round | 01/03/1997 | Sheffield Wednesday | - | Middlesbrough FC | 3:1 | |
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| 27. Round | 05/03/1997 | Middlesbrough FC | - | Derby County | 6:1 | ||||
| 30. Round | 19/03/1997 | Middlesbrough FC | - | Blackburn Rovers | 2:1 | ||||
| 32. Round | 22/03/1997 | Middlesbrough FC | - | Chelsea FC | 1:0 | |
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| 34. Round | 24/03/1997 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 33. Round | 09/04/1997 | West Ham United | - | Middlesbrough FC | 0:0 | |
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| 37. Round | 03/05/1997 | Middlesbrough FC | - | Aston Villa | 3:2 | ||||
| 26. Round | 05/05/1997 | Manchester United | - | Middlesbrough FC | 3:3 | ||||
| 18. Round | 08/05/1997 | Blackburn Rovers | - | Middlesbrough FC | 0:0 | |
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| 38. Round | 11/05/1997 | Leeds United | - | Middlesbrough FC | 1:1 |
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