4. Round | 21/08/1999 | Leeds United | - | Sunderland AFC | 2:1 | ||||
17. Round | 04/12/1999 | Sunderland AFC | - | Chelsea FC | 4:1 | ||||
23. Round | 23/01/2000 | Sunderland AFC | - | Leeds United | 1:2 | ||||
25. Round | 12/02/2000 | Coventry City | - | Sunderland AFC | 3:2 | ||||
26. Round | 26/02/2000 | Sunderland AFC | - | Derby County | 1:1 | ||||
27. Round | 05/03/2000 | Leicester City | - | Sunderland AFC | 5:2 | ||||
28. Round | 11/03/2000 | Liverpool FC | - | Sunderland AFC | 1:1 | ||||
29. Round | 18/03/2000 | Sunderland AFC | - | Middlesbrough FC | 1:1 | ||||
30. Round | 25/03/2000 | Sunderland AFC | - | Everton FC | 2:1 | ||||
31. Round | 01/04/2000 | Southampton FC | - | Sunderland AFC | 1:2 | ||||
32. Round | 08/04/2000 | Sunderland AFC | - | Wimbledon FC | 2:1 | ||||
33. Round | 15/04/2000 | Manchester United | - | Sunderland AFC | 4:0 | ||||
34. Round | 22/04/2000 | Sheffield Wednesday | - | Sunderland AFC | 0:2 | ||||
37. Round | 06/05/2000 | Sunderland AFC | - | West Ham United | 1:0 | ||||
38. Round | 14/05/2000 | Tottenham Hotspur | - | Sunderland AFC | 3:1 |