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League Cup
Below are the Worthington Cup first round (first and second leg) results for the 1999-2000 season.
| First Round, 1st Leg | Score | |
| Birmingham City | Exeter United |
3-0 |
| Blackpool | Tranmere Rovers | 2-1 |
| Bournemouth | Barnet | 2-0 |
| Bury | Notts County | 1-0 |
| Cambridge United | Bristol City | 2-2 |
| Cardiff City | Queens Park Rangers | 1-2 |
| Carlisle United | Grimsby Town | 0-0 |
| Chester | Port Vale | 2-1 |
| Colchester United | Crystal Palace | 2-2 |
| Darlington | Bolton Wanderers | 1-1 |
| Halifax Town | West Bromwich Albion | 0-0 |
| Hartlepool United | Crewe | 3-3 |
| Lincoln City | Barnsley | 2-4 |
| Luton Town | Bristol Rovers | 0-2 |
| Macclesfield | Stoke City | 1-1 |
| Northampton Town | Fulham | 1-2 |
| Norwich City | Cheltenham | 2-0 |
| Preston North End | Wrexham | 1-0 |
| Rochdale | Chesterfield | 1-2 |
| Rotherham United | Hull City | 0-1 |
| Scunthorpe United | Huddersfield Town | 0-2 |
| Sheffield United | Shrewsbury Town | 3-0 |
| Southend United | Oxford United | 0-2 |
| Stockport County | Oldham Athletic | 2-0 |
| Swindon Town | Leyton Orient | 0-1 |
| Walsall | Plymouth Argyle | 4-1 |
| Wycombe Wanderers | Wolverhampton Wanderers | 0-1 |
| York City | Wigan Athletic | 0-1 |
| Brentford | Ipswich Town | 0-2 |
| Brighton & Hove Albion | Gillingham | 0-2 |
| Manchester City | Burnley | 5-0 |
| Nottingham Forest | Mansfield Town | 3-0 |
| Reading | Peterborough United | 0-0 |
| Swansea City | Millwall | 2-0 |
|
First Round, 2nd Leg |
Score |
Aggregate Score |
|
| Barnet | Bournemouth | 3-2 |
Bournemouth won 4-3 |
| Barnsley | Lincoln City | 2-2 | Barnsley won 6-4 |
| Bolton Wanderers | Darlington | 5-3 | Bolton won 6-4 |
| Bristol City | Cambridge United | 2-1 | Bristol City won 4-3 |
| Bristol Rovers | Luton Town | 2-2 | Bristol Rovers won 4-2 |
| Burnley | Manchester City | 1-0 | Man City won 6-0 |
| Cheltenham | Norwich City | 2-1 (aet) | Norwich won 3-2 |
| Chesterfield | Rochdale | 2-1 | Chesterfield won 5-1 |
| Crewe | Hartlepool United | 1-0 | Crewe won 4-3 |
| Crystal Palace | Colchester United | 3-1 | C.Palace won 5-3 |
| Exeter United | Birmingham City | 1-2 | Birmingham won 5-1 |
| Fulham | Northampton Town | 3-1 | Fulham won 5-2 |
| Gillingham | Brighton & Hove Albion | 2-0 | Gillingham won 4-0 |
| Grimsby Town | Carlisle United | 6-0 | Grimsby won 6-0 |
| Huddersfield Town | Scunthorpe United | 0-0 | Huddersfield won 2-0 |
| Hull City | Rotherham United | 2-0 | Hull won 3-0 |
| Ipswich Town | Brentford | 2-0 | Ipswich won 4-0 |
| Leyton Orient | Swindon Town | 1-1 | Leyton Orient won 2-1 |
| Mansfield Town | Nottingham Forest | 1-0 | Nott'm For won 3-1 |
| Millwall | Swansea City | 1-1 | Swansea won 3-1 |
| Notts County | Bury | 2-0 | Notts County won 2-1 |
| Oldham Athletic | Stockport County | 1-1 | Stockport won 3-1 |
| Oxford United | Southend United | 1-0 | Oxford Utd won 3-0 |
| Peterborough United | Reading | 1-2 | Reading won 2-1 |
| Plymouth Argyle | Walsall | 1-4 | Walsall won 8-2 |
| Port Vale | Chester | 4-4 | Chester won 6-5 |
| Queens Park Rangers | Cardiff City | 1-2 | Cardiff won 3-2 on pens |
| Shrewsbury Town | Sheffield United | 0-3 | Sheff Utd won 6-0 |
| Stoke City | Macclesfield | 3-0 | Stoke won 4-1 |
| Tranmere Rovers | Blackpool | 3-1 | Tranmere won 4-3 |
| West Bromwich Albion | Halifax Town | 5-1 | West Brom won 5-1 |
| Wigan Athletic | York City | 2-0 | Wigan won 3-0 |
| Wolverhampton Wanderers | Wycombe Wanderers | 2-4 | Wycombe won 4-3 |
| Wrexham | Preston North End | 0-2 |
Preston won 3-0 |