| 2. Round | 14/09/1998 | Brentford FC | - | Tottenham Hotspur | 2:3 | ||||
| 2. Round | 22/09/1998 | Tottenham Hotspur | - | Brentford FC | 3:2 |  |
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| 3. Round | 26/10/1998 | Northampton Town | - | Tottenham Hotspur | 1:3 | ||||
| Round of 16 | 09/11/1998 | Liverpool FC | - | Tottenham Hotspur | 1:3 | ||||
| Quarter-finals | 01/12/1998 | Tottenham Hotspur | - | Manchester United | 3:1 |  |
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| Semi-finals | 26/01/1999 | Tottenham Hotspur | - | Wimbledon FC | 0:0 | ||||
| Semi-finals | 15/02/1999 | Wimbledon FC | - | Tottenham Hotspur | 0:1 | ||||
| Final | 20/03/1999 | Leicester City | - | Tottenham Hotspur | 0:1 |
France
