1. Round | 07/08/1999 | Arsenal FC | - | Leicester City | 2:1 | ||||
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 | ||||
6. Round | 28/08/1999 | Liverpool FC | - | Arsenal FC | 2:0 | ||||
7. Round | 11/09/1999 | Arsenal FC | - | Aston Villa | 3:1 | ||||
8. Round | 18/09/1999 | Southampton FC | - | Arsenal FC | 0:1 | ||||
9. Round | 25/09/1999 | Arsenal FC | - | Watford FC | 1:0 | ||||
16. Round | 28/11/1999 | Arsenal FC | - | Derby County | 2:1 | ||||
17. Round | 04/12/1999 | Leicester City | - | Arsenal FC | 0:3 | ||||
18. Round | 18/12/1999 | Arsenal FC | - | Wimbledon FC | 1:1 | ||||
28. Round | 12/03/2000 | Middlesbrough FC | - | Arsenal FC | 2:1 | ||||
29. Round | 19/03/2000 | Arsenal FC | - | Tottenham Hotspur | 2:1 | ||||
38. Round | 14/05/2000 | Newcastle United | - | Arsenal FC | 4:2 |