2. Round | 10/08/1999 | Derby County | - | Arsenal FC | 1:2 | ||||
3. Round | 14/08/1999 | Sunderland AFC | - | Arsenal FC | 0:0 | ||||
4. Round | 22/08/1999 | Arsenal FC | - | Manchester United | 1:2 | ||||
5. Round | 25/08/1999 | Arsenal FC | - | Bradford City | 2:0 | ||||
13. Round | 30/10/1999 | Arsenal FC | - | Newcastle United | 0:0 | ||||
15. Round | 20/11/1999 | Arsenal FC | - | Middlesbrough FC | 5:1 | ||||
16. Round | 28/11/1999 | Arsenal FC | - | Derby County | 2:1 | ||||
17. Round | 04/12/1999 | Leicester City | - | Arsenal FC | 0:3 |