11. Round | 18/10/1999 | Sunderland AFC | - | Aston Villa | 2:1 | ||||
14. Round | 06/11/1999 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
15. Round | 20/11/1999 | Sunderland AFC | - | Liverpool FC | 0:2 | ||||
16. Round | 27/11/1999 | Watford FC | - | Sunderland AFC | 2:3 | ||||
19. Round | 26/12/1999 | Everton FC | - | Sunderland AFC | 5:0 | ||||
20. Round | 28/12/1999 | Sunderland AFC | - | Manchester United | 2:2 | ||||
23. Round | 23/01/2000 | Sunderland AFC | - | Leeds United | 1:2 | ||||
24. Round | 05/02/2000 | Sunderland AFC | - | Newcastle United | 2:2 |