2. Round | 10/08/1999 | Sunderland AFC | - | Watford FC | 2:0 | ||||
7. Round | 11/09/1999 | Sunderland AFC | - | Leicester City | 2:0 | ||||
8. Round | 18/09/1999 | Derby County | - | Sunderland AFC | 0:5 | ||||
9. Round | 25/09/1999 | Sunderland AFC | - | Sheffield Wednesday | 1:0 | ||||
10. Round | 02/10/1999 | Bradford City | - | Sunderland AFC | 0:4 | ||||
12. Round | 24/10/1999 | West Ham United | - | Sunderland AFC | 1:1 | ||||
13. Round | 31/10/1999 | Sunderland AFC | - | Tottenham Hotspur | 2:1 | ||||
34. Round | 22/04/2000 | Sheffield Wednesday | - | Sunderland AFC | 0:2 | ||||
35. Round | 24/04/2000 | Sunderland AFC | - | Bradford City | 0:1 | ||||
37. Round | 06/05/2000 | Sunderland AFC | - | West Ham United | 1:0 |