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League Cup
Below are the Worthington Cup forth round results for the 1999-2000 season.
| Fourth Round | Score | |
| Aston Villa | Southampton | 4-0 |
| Birmingham City | West Ham United | 2-3 |
| Bolton Wanderers | Sheffield Wednesday | 1-0 |
| Fulham | Tottenham Hotspur | 3-1 |
| Huddersfield Town | Wimbledon | 1-2 aet |
| Leeds United | Leicester City | 0-0 |
|
Leicester City win 4-2 on penalties |
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| Middlesbrough | Arsenal | 2-2 aet |
|
Middlesbrough win 3-1 on penalties |
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| Tranmere Rovers | Barnsley | 4-0 |