| 2. Runde | 27.09.1988 | Notts County | - | Tottenham Hotspur | 1:1 |  |
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| 2. Runde | 11.10.1988 | Tottenham Hotspur | - | Notts County | 2:1 |  |
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| 3. Runde | 01.11.1988 | Tottenham Hotspur | - | Blackburn Rovers | 0:0 | ||||
| 3. Runde | 09.11.1988 | Blackburn Rovers | - | Tottenham Hotspur | 1:2 n.V. | ||||
| Achtelfinale | 29.11.1988 | Southampton FC | - | Tottenham Hotspur | 2:1 |
England