9. Round | 17/10/1998 | Middlesbrough FC | - | Blackburn Rovers | 2:1 | ||||
10. Round | 24/10/1998 | Wimbledon FC | - | Middlesbrough FC | 2:2 | ||||
14. Round | 21/11/1998 | Middlesbrough FC | - | Coventry City | 2:0 | ||||
25. Round | 17/02/1999 | Everton FC | - | Middlesbrough FC | 5:0 | ||||
31. Round | 03/04/1999 | Blackburn Rovers | - | Middlesbrough FC | 0:0 | ||||
32. Round | 05/04/1999 | Middlesbrough FC | - | Wimbledon FC | 3:1 | ||||
35. Round | 24/04/1999 | Middlesbrough FC | - | Arsenal FC | 1:6 | ||||
36. Round | 01/05/1999 | Newcastle United | - | Middlesbrough FC | 1:1 | ||||
37. Round | 09/05/1999 | Middlesbrough FC | - | Manchester United | 0:1 | ||||
38. Round | 16/05/1999 | West Ham United | - | Middlesbrough FC | 4:0 |