| 12. Round | 17/10/1992 | Tottenham Hotspur | - | Middlesbrough FC | 2:2 | ||||
| 4. Round | 21/10/1992 | Nottingham Forest | - | Middlesbrough FC | 1:0 | ||||
| 13. Round | 24/10/1992 | Middlesbrough FC | - | Sheffield Wednesday | 1:1 | ||||
| 14. Round | 30/10/1992 | Norwich City | - | Middlesbrough FC | 1:1 | ||||
| 15. Round | 06/11/1992 | Liverpool FC | - | Middlesbrough FC | 4:1 | ||||
| 16. Round | 20/11/1992 | Middlesbrough FC | - | Wimbledon FC | 2:0 | ||||
| 17. Round | 27/11/1992 | Oldham Athletic | - | Middlesbrough FC | 4:1 | ||||
| 18. Round | 04/12/1992 | Middlesbrough FC | - | Blackburn Rovers | 3:2 | ||||
| 20. Round | 18/12/1992 | Arsenal FC | - | Middlesbrough FC | 1:1 | ||||
| 22. Round | 27/12/1992 | Middlesbrough FC | - | Crystal Palace | 0:1 | ||||
| 28. Round | 08/02/1993 | Sheffield United | - | Middlesbrough FC | 2:0 |
England