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 | ||||
8. Round | 19/09/1999 | Newcastle United | - | Sheffield Wednesday | 8:0 | ||||
9. Round | 25/09/1999 | Leeds United | - | Newcastle United | 3:2 | ||||
16. Round | 28/11/1999 | Newcastle United | - | Tottenham Hotspur | 2:1 | ||||
36. Round | 29/04/2000 | Newcastle United | - | Coventry City | 2:0 | ||||
35. Round | 02/05/2000 | Middlesbrough FC | - | Newcastle United | 2:2 | ||||
38. Round | 14/05/2000 | Newcastle United | - | Arsenal FC | 4:2 |