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League Cup
Below are the Worthington Cup fifth round results for the 1999-2000 season.
| Fifth Round | Score | |
| Bolton Wanderers | Wimbledon | 2-1 |
| Leicester City | Fulham | 3-3 |
|
Leicester City win 3-0 on Penalties |
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| Tranmere Rovers | Middlesbrough | 2-1 |
| West Ham United | Aston Villa | 2-2* |
|
West Ham United win 5-4
on Penalties |
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| West Ham United | Aston Villa | 1-3 |