4. Ronde | 09.09.1998 | Leicester City | - | Middlesbrough FC | 0:1 | ||||
8. Ronde | 03.10.1998 | Middlesbrough FC | - | Sheffield Wednesday | 4:0 | ||||
25. Ronde | 17.02.1999 | Everton FC | - | Middlesbrough FC | 5:0 | ||||
26. Ronde | 20.02.1999 | Middlesbrough FC | - | Tottenham Hotspur | 0:0 | ||||
29. Ronde | 14.03.1999 | Middlesbrough FC | - | Southampton FC | 3:0 | ||||
37. Ronde | 09.05.1999 | Middlesbrough FC | - | Manchester United | 0:1 | ||||
38. Ronde | 16.05.1999 | West Ham United | - | Middlesbrough FC | 4:0 |