| 12. Round | 04/11/1995 | Middlesbrough FC | - | Leeds United | 1:1 | ||||
| 13. Round | 18/11/1995 | Wimbledon FC | - | Middlesbrough FC | 0:0 | ||||
| 14. Round | 21/11/1995 | Middlesbrough FC | - | Tottenham Hotspur | 0:1 | ||||
| 15. Round | 25/11/1995 | Middlesbrough FC | - | Liverpool FC | 2:1 | ||||
| 16. Round | 02/12/1995 | Queens Park Rangers | - | Middlesbrough FC | 1:1 | ||||
| 17. Round | 09/12/1995 | Middlesbrough FC | - | Manchester City | 4:1 |  |
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| 18. Round | 16/12/1995 | Blackburn Rovers | - | Middlesbrough FC | 1:0 | ||||
| 20. Round | 26/12/1995 | Everton FC | - | Middlesbrough FC | 4:0 | ||||
| 21. Round | 30/12/1995 | Nottingham Forest | - | Middlesbrough FC | 1:0 | |
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| 22. Round | 01/01/1996 | Middlesbrough FC | - | Aston Villa | 0:2 | ||||
| 23. Round | 13/01/1996 | Middlesbrough FC | - | Arsenal FC | 2:3 | ||||
| 25. Round | 04/02/1996 | Chelsea FC | - | Middlesbrough FC | 5:0 | |
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| 26. Round | 10/02/1996 | Middlesbrough FC | - | Newcastle United | 1:2 |
England