| 2. Runde | 28.09.1988 | Leicester City | - | Watford FC | 4:1 |  |
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| 2. Runde | 11.10.1988 | Watford FC | - | Leicester City | 2:2 | ||||
| 3. Runde | 02.11.1988 | Leicester City | - | Norwich City | 2:0 | ||||
| Achtelfinale | 30.11.1988 | Leicester City | - | Nottingham Forest | 0:0 | ||||
| Achtelfinale | 14.12.1988 | Nottingham Forest | - | Leicester City | 2:1 |
Schottland