2. Round | 10/08/1999 | Sunderland AFC | - | Watford FC | 2:0 | ||||
3. Round | 14/08/1999 | Sunderland AFC | - | Arsenal FC | 0:0 | ||||
6. Round | 29/08/1999 | Sunderland AFC | - | Coventry City | 1:1 | ||||
21. Round | 03/01/2000 | Wimbledon FC | - | Sunderland AFC | 1:0 | ||||
27. Round | 05/03/2000 | Leicester City | - | Sunderland AFC | 5:2 | ||||
34. Round | 22/04/2000 | Sheffield Wednesday | - | Sunderland AFC | 0:2 | ||||
35. Round | 24/04/2000 | Sunderland AFC | - | Bradford City | 0:1 | ||||
36. Round | 29/04/2000 | Aston Villa | - | Sunderland AFC | 1:1 | ||||
37. Round | 06/05/2000 | Sunderland AFC | - | West Ham United | 1:0 | ||||
38. Round | 14/05/2000 | Tottenham Hotspur | - | Sunderland AFC | 3:1 |