| 8. Round | 19/09/1999 | Newcastle United | - | Sheffield Wednesday | 8:0 | ||||
| 10. Round | 03/10/1999 | Newcastle United | - | Middlesbrough FC | 2:1 | ||||
| 16. Round | 28/11/1999 | Newcastle United | - | Tottenham Hotspur | 2:1 |  |
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| 18. Round | 18/12/1999 | Bradford City | - | Newcastle United | 2:0 | ||||
| 19. Round | 26/12/1999 | Newcastle United | - | Liverpool FC | 2:2 | ||||
| 21. Round | 03/01/2000 | Newcastle United | - | West Ham United | 2:2 |
Scotland
