1. Round | 07/08/1999 | Newcastle United | - | Aston Villa | 0:1 | ||||
2. Round | 09/08/1999 | Tottenham Hotspur | - | Newcastle United | 3:1 | ||||
3. Round | 15/08/1999 | Southampton FC | - | Newcastle United | 4:2 | ||||
4. Round | 21/08/1999 | Newcastle United | - | Wimbledon FC | 3:3 | ||||
5. Round | 25/08/1999 | Newcastle United | - | Sunderland AFC | 1:2 | ||||
6. Round | 30/08/1999 | Manchester United | - | Newcastle United | 5:1 | ||||
7. Round | 11/09/1999 | Chelsea FC | - | Newcastle United | 1:0 | ||||
8. Round | 19/09/1999 | Newcastle United | - | Sheffield Wednesday | 8:0 | ||||
9. Round | 25/09/1999 | Leeds United | - | Newcastle United | 3:2 | ||||
10. Round | 03/10/1999 | Newcastle United | - | Middlesbrough FC | 2:1 | ||||
30. Round | 25/03/2000 | Liverpool FC | - | Newcastle United | 2:1 | ||||
31. Round | 01/04/2000 | Newcastle United | - | Bradford City | 2:0 | ||||
32. Round | 12/04/2000 | West Ham United | - | Newcastle United | 2:1 | ||||
33. Round | 15/04/2000 | Newcastle United | - | Leicester City | 0:2 |