| 11. Round | 26/10/1996 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
| 12. Round | 03/11/1996 | Newcastle United | - | Middlesbrough FC | 3:1 | ||||
| 13. Round | 17/11/1996 | Derby County | - | Middlesbrough FC | 2:1 | ||||
| 14. Round | 23/11/1996 | Middlesbrough FC | - | Manchester United | 2:2 | ||||
| 15. Round | 30/11/1996 | Aston Villa | - | Middlesbrough FC | 1:0 | ||||
| 17. Round | 03/12/1996 | Middlesbrough FC | - | Leicester City | 0:2 | ||||
| 16. Round | 07/12/1996 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
| 24. Round | 14/12/1996 | Liverpool FC | - | Middlesbrough FC | 5:1 | ||||
| 19. Round | 26/12/1996 | Middlesbrough FC | - | Everton FC | 4:2 | ||||
| 20. Round | 28/12/1996 | Coventry City | - | Middlesbrough FC | 3:0 | ||||
| 21. Round | 01/01/1997 | Arsenal FC | - | Middlesbrough FC | 2:0 | ||||
| 22. Round | 11/01/1997 | Middlesbrough FC | - | Southampton FC | 0:1 |
England