1. Round | 07/08/1999 | West Ham United | - | Tottenham Hotspur | 1:0 | ||||
2. Round | 09/08/1999 | Tottenham Hotspur | - | Newcastle United | 3:1 | ||||
3. Round | 14/08/1999 | Tottenham Hotspur | - | Everton FC | 3:2 | ||||
4. Round | 21/08/1999 | Sheffield Wednesday | - | Tottenham Hotspur | 1:2 | ||||
6. Round | 28/08/1999 | Tottenham Hotspur | - | Leeds United | 1:2 | ||||
7. Round | 12/09/1999 | Bradford City | - | Tottenham Hotspur | 1:1 | ||||
27. Round | 04/03/2000 | Tottenham Hotspur | - | Bradford City | 1:1 | ||||
29. Round | 19/03/2000 | Arsenal FC | - | Tottenham Hotspur | 2:1 | ||||
30. Round | 25/03/2000 | Watford FC | - | Tottenham Hotspur | 1:1 |