3. Round | 23/08/1996 | Nottingham Forest | - | Middlesbrough FC | 1:1 | ||||
4. Round | 03/09/1996 | Middlesbrough FC | - | West Ham United | 4:1 | ||||
5. Round | 06/09/1996 | Middlesbrough FC | - | Coventry City | 4:0 | ||||
6. Round | 13/09/1996 | Everton FC | - | Middlesbrough FC | 1:2 | ||||
7. Round | 20/09/1996 | Middlesbrough FC | - | Arsenal FC | 0:2 | ||||
8. Round | 27/09/1996 | Southampton FC | - | Middlesbrough FC | 4:0 | ||||
9. Round | 13/10/1996 | Sunderland AFC | - | Middlesbrough FC | 2:2 | ||||
16. Round | 06/12/1996 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
20. Round | 13/12/1996 | Liverpool FC | - | Middlesbrough FC | 5:1 |