1. Round | 07/08/1999 | Chelsea FC | - | Sunderland AFC | 4:0 | ||||
3. Round | 14/08/1999 | Sunderland AFC | - | Arsenal FC | 0:0 | ||||
4. Round | 21/08/1999 | Leeds United | - | Sunderland AFC | 2:1 | ||||
5. Round | 25/08/1999 | Newcastle United | - | Sunderland AFC | 1:2 | ||||
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 | ||||
11. Round | 18/10/1999 | Sunderland AFC | - | Aston Villa | 2:1 | ||||
13. Round | 31/10/1999 | Sunderland AFC | - | Tottenham Hotspur | 2:1 | ||||
14. Round | 06/11/1999 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
16. Round | 27/11/1999 | Watford FC | - | Sunderland AFC | 2:3 |