1. Round | 20/08/1995 | Arsenal FC | - | Middlesbrough FC | 1:1 | ||||
3. Round | 26/08/1995 | Middlesbrough FC | - | Chelsea FC | 2:0 | ||||
4. Round | 30/08/1995 | Newcastle United | - | Middlesbrough FC | 1:0 | ||||
35. Round | 08/04/1996 | Tottenham Hotspur | - | Middlesbrough FC | 1:1 | ||||
36. Round | 13/04/1996 | Middlesbrough FC | - | Wimbledon FC | 1:2 | ||||
37. Round | 27/04/1996 | Liverpool FC | - | Middlesbrough FC | 1:0 |