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League Cup
Below are the Worthington Cup third round results for the 1999-2000 season.
| Third Round | Score | |
| Arsenal | Preston North End | 2-1 |
| Aston Villa | Manchester United | 3-0 |
| Birmingham City | Newcastle United | 2-0 |
| Bradford City | Barnsley | 2-3 |
| Chelsea | Huddersfield Town | 0-1 |
| Derby County | Bolton Wanderers | 1-2 |
| Leeds United | Blackburn Rovers | 1-0 |
| Leicester City | Grimsby Town | 2-0 |
| Middlesbrough | Watford | 1-0 |
| Sheffield Wednesday | Nottingham Forest | 4-1 |
| Southampton | Liverpool | 2-1 |
| Tottenham Hotspur | Crewe Alexandra | 3-1 |
| Tranmere Rovers | Oxford United | 2-0 |
| West Bromwich Albion | Fulham | 1-2 |
| West Ham United | Bournemouth | 2-0 |
| Wimbledon | Sunderland | 3-2 |