30. Round | 24/03/1989 | Wimbledon FC | - | Middlesbrough FC | 1:1 | ||||
31. Round | 26/03/1989 | Middlesbrough FC | - | Everton FC | 3:3 | ||||
32. Round | 31/03/1989 | Charlton Athletic | - | Middlesbrough FC | 2:0 | ||||
37. Round | 05/05/1989 | Middlesbrough FC | - | Arsenal FC | 0:1 |