| 2. Round | 04/10/1989 | Southend United | - | Tottenham Hotspur | 3:2 aet |  |
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| 3. Round | 25/10/1989 | Manchester United | - | Tottenham Hotspur | 0:3 | |
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| Quarter-finals | 17/01/1990 | Nottingham Forest | - | Tottenham Hotspur | 2:2 | ||||
| Quarter-finals | 24/01/1990 | Tottenham Hotspur | - | Nottingham Forest | 2:3 | |
Spain