5. Ronde | 24.08.1999 | Middlesbrough FC | - | Leicester City | 0:3 | ||||
17. Ronde | 04.12.1999 | Bradford City | - | Middlesbrough FC | 1:1 | ||||
18. Ronde | 18.12.1999 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
19. Ronde | 26.12.1999 | Sheffield Wednesday | - | Middlesbrough FC | 1:0 | ||||
22. Ronde | 15.01.2000 | Middlesbrough FC | - | Derby County | 1:4 | ||||
21. Ronde | 29.01.2000 | Manchester United | - | Middlesbrough FC | 1:0 | ||||
25. Ronde | 14.02.2000 | Middlesbrough FC | - | Aston Villa | 0:4 | ||||
20. Ronde | 19.02.2000 | Middlesbrough FC | - | Coventry City | 2:0 | ||||
26. Ronde | 26.02.2000 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
27. Ronde | 04.03.2000 | Southampton FC | - | Middlesbrough FC | 1:1 | ||||
28. Ronde | 12.03.2000 | Middlesbrough FC | - | Arsenal FC | 2:1 | ||||
29. Ronde | 18.03.2000 | Sunderland AFC | - | Middlesbrough FC | 1:1 | ||||
38. Ronde | 14.05.2000 | Everton FC | - | Middlesbrough FC | 0:2 |