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League Cup
Below are the Worthington Cup second round (first and second leg) results for the 1999-2000 season.
| Second Round, 1st Leg | Score | |
| Barnsley | Stockport County |
1-1 |
| Birmingham City | Bristol Rovers | 2-0 |
| Bradford City | Reading | 1-1 |
| Cardiff City | Wimbledon | 1-1 |
| Charlton Athletic | Bournemouth | 0-0 |
| Chester | Aston Villa | 0-1 |
| Chesterfield United | Middlesbrough | 0-0 |
| Crewe Alexandra | Ipswich Town | 2-1 |
| Crystal Palace | Leicester City | 3-3 |
| Gillingham | Bolton Wanderers | 1-4 |
| Grimsby Town | Leyton Orient | 4-1 |
| Huddersfield Town | Notts County | 2-1 |
| Hull City | Liverpool | 1-5 |
| Manchester City | Southampton | 0-0 |
| Norwich City | Fulham | 0-4 |
| Nottingham Forest | Bristol City | 2-1 |
| Oxford United | Everton | 1-1 |
| Portsmouth | Blackburn Rovers | 0-3 |
| Sheffield United | Preston North End | 2-0 |
| Stoke City | Sheffield Wednesday | 0-0 |
| Sunderland | Walsall | 3-2 |
| Swansea City | Derby County | 0-0 |
| Tranmere Rovers | Coventry City | 5-1 |
| Watford | Wigan Athletic | 2-0 |
| West Bromwich Albion | Wycombe Wanderers | 0-0 |
|
Second Round, 2nd Leg |
Score |
Aggregate Score |
|
| Aston Villa | Chester | 5-0 |
Aston Villa won 6-0 |
| Blackburn Rovers | Portsmouth | 3-1 | Blackburn won 6-1 |
| Bolton Wanderers | Gillingham | 2-0 | Bolton won 6-1 |
| Bournemouth | Charlton Athletic | 0-0 | Bmth won 3-1 on pens |
| Bristol City | Nottingham Forest | 0-0 | Notts Forest won 2-1 |
| Bristol Rovers | Birmingham City | 0-1 | Birmingham won 3-0 |
| Coventry City | Tranmere Rovers | 3-1 | Tranmere won 6-4 |
| Derby County | Swansea City | 3-1 | Derby won 3-1 |
| Everton | Oxford United | 0-1 | Oxford won 2-1 |
| Fulham | Norwich City | 2-0 | Fulham won 6-0 |
| Ipswich Town | Crewe Alexandra | 1-1 | Crewe won 3-2 |
| Leicester City | Crystal Palace | 4-2 | Leicester won 7-5 |
| Leyton Orient | Grimsby Town | 1-0 | Grimsby won 4-2 |
| Liverpool | Hull City | 4-2 | Liverpool won 9-3 |
| Middlesbrough | Chesterfield United | 2-1 | Middlesbrough won 2-1 |
| Notts County | Huddersfield Town | 2-2 | Huddersfield won 4-3 |
| Preston North End | Sheffield United | 3-0 | Preston won 3-2 |
| Reading | Bradford City | 2-2 (aet) | Brad won on away goals |
| Sheffield Wednesday | Stoke City | 3-1 | Sheff Wed won 3-1 |
| Southampton | Manchester City | 4-3 | Southampton won 4-3 |
| Stockport County | Barnsley | 3-3 (aet) | Barn won on away goals |
| Walsall | Sunderland | 0-5 | Sunderland won 8-2 |
| Wigan Athletic | Watford | 3-1 (aet) | Wat won on away goals |
| Wimbledon | Cardiff City | 3-1 | Wimbledon won 4-2 |
| Wycombe Wanderers | West Bromwich Albion | 3-4 | West Brom won 5-4 |