| 3. Round | 01/01/1999 | Tottenham Hotspur | - | Watford FC | 5:2 | ||||
| 4. Round | 22/01/1999 | Wimbledon FC | - | Tottenham Hotspur | 1:1 | ||||
| 4. Round | 01/02/1999 | Tottenham Hotspur | - | Wimbledon FC | 3:0 | ||||
| Round of 16 | 12/02/1999 | Leeds United | - | Tottenham Hotspur | 1:1 |  |
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| Round of 16 | 23/02/1999 | Tottenham Hotspur | - | Leeds United | 2:0 | ||||
| Quarter-finals | 15/03/1999 | Barnsley FC | - | Tottenham Hotspur | 0:1 | ||||
| Semi-finals | 10/04/1999 | Newcastle United | - | Tottenham Hotspur | 2:0 aet |
England
