| 1. Round | 07/08/1999 | Newcastle United | - | Aston Villa | 0:1 |  |
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| 2. Round | 09/08/1999 | Tottenham Hotspur | - | Newcastle United | 3:1 | |
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| 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 | |
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| 30. Round | 25/03/2000 | Liverpool FC | - | Newcastle United | 2:1 | |
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| 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 |
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