| 2. Round | 19/09/1989 | Tottenham Hotspur | - | Southend United | 1:0 | ||||
| 2. Round | 04/10/1989 | Southend United | - | Tottenham Hotspur | 3:2 aet | ||||
| 3. Round | 25/10/1989 | Manchester United | - | Tottenham Hotspur | 0:3 | ||||
| Round of 16 | 29/11/1989 | Tottenham Hotspur | - | Tranmere Rovers | 4:0 | ||||
| Quarter-finals | 17/01/1990 | Nottingham Forest | - | Tottenham Hotspur | 2:2 | ||||
| Quarter-finals | 24/01/1990 | Tottenham Hotspur | - | Nottingham Forest | 2:3 |
Belgium