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| Littlewoods
    Cup 1989/90 Results | |||||||||||
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| 
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| First Round | |||||||||||
| Byes
    - The 20 First Division 
  clubs plus the 3 clubs relegated from the First Division in 1988/89 (Middlesbrough, 
  Newcastle and West Ham United) plus the top 13 sides in the 1988/89 Second 
  Division table who had not been promoted to the First Division (Barnsley, 
  Blackburn, Bournemouth, Bradford City, Ipswich, Leeds, Leicester, Oldham, 
  Stoke, Sunderland, Swindon, Watford, WBA).    | |||||||||||
| Tue | Aug | 22 | Birmingham City | 2 | - | 1 | Chesterfield | ||||
| Tue | Aug | 29 | Chesterfield | 1 | - | 1 | Birmingham City | ||||
| Birmingham won 3-2 on aggregate | |||||||||||
| Tue | Aug | 22 | Blackpool | 2 | - | 2 | Burnley | ||||
| Tue | Aug | 29 | Burnley | 0 | - | 1 | Blackpool | ||||
| Blackpool won 3-2 on aggregate | |||||||||||
| Wed | Aug | 23 | Brighton & Hove Albion | 0 | - | 3 | Brentford | ||||
| Tue | Aug | 29 | Brentford | 1 | - | 1 | Brighton & Hove Albion | ||||
| Brentford won 4-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Bristol City | 2 | - | 3 | Reading | ||||
| Tue | Aug | 29 | Reading | 2 | - | 2 | Bristol City | ||||
| Reading won 5-4 on aggregate | |||||||||||
| Wed | Aug | 23 | Bristol Rovers | 1 | - | 0 | Portsmouth | ||||
| Tue | Aug | 29 | Portsmouth | 2 | - | 0 | Bristol Rovers | ||||
| Portsmouth won 2-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Cambridge United | 3 | - | 1 | Maidstone United | ||||
| Wed | Aug | 30 | Maidstone United | 0 | - | 1 | Cambridge United | ||||
| Cambridge United won 4-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Cardiff City | 0 | - | 3 | Plymouth Argyle | ||||
| Tue | Aug | 29 | Plymouth Argyle | 0 | - | 2 | Cardiff City | ||||
| Plymouth won 3-2 on aggregate | |||||||||||
| Tue | Aug | 22 | Colchester United | 3 | - | 4 | Southend United | ||||
| Tue | Aug | 29 | Southend United | 2 | - | 1 | Colchester United | ||||
| Southend won 6-4 on aggregate | |||||||||||
| Tue | Aug | 22 | Crewe Alexandra | 4 | - | 0 | Chester City | ||||
| Tue | Aug | 29 | Chester City | 0 | - | 2 | Crewe Alexandra | ||||
| Crewe won 6-0 on aggregate | |||||||||||
| Wed | Aug | 23 | Exeter City | 3 | - | 0 | Swansea City | ||||
| Tue | Aug | 29 | Swansea City | 1 | - | 1 | Exeter City | ||||
| Exeter won 4-1 on aggregate | |||||||||||
| Wed | Aug | 23 | Fulham | 0 | - | 1 | Oxford United | ||||
| Wed | Aug | 30 | Oxford United | 3 | - | 5 | Fulham | ||||
| Fulham won 5-4 on aggregate | |||||||||||
| Tue | Aug | 22 | Gillingham | 1 | - | 4 | Leyton Orient | ||||
| Tue | Aug | 29 | Leyton Orient | 3 | - | 0 | Gillingham | ||||
| Leyton Orient won 7-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Halifax Town | 3 | - | 1 | Carlisle United | ||||
| Tue | Aug | 29 | Carlisle United | 1 | - | 0 | Halifax Town | ||||
| Halifax won 3-2 on aggregate | |||||||||||
| Wed | Aug | 23 | Hartlepool United | 3 | - | 3 | York City | ||||
| Tue | Aug | 29 | York City | 4 | - | 1 | Hartlepool United | ||||
| York won 7-4 on aggregate | |||||||||||
| Tue | Aug | 22 | Huddersfield Town | 1 | - | 1 | Doncaster Rovers | ||||
| Tue | Aug | 29 | Doncaster Rovers | 1 | - | 2 | Huddersfield Town | ||||
| Huddersfield won 3-2 on aggregate | |||||||||||
| Tue | Aug | 22 | Hull City | 1 | - | 0 | Grimsby Town | ||||
| Tue | Aug | 29 | Grimsby Town | 2 | - | 0 | Hull City | ||||
| Grimsby won 2-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Mansfield Town | 1 | - | 1 | Northampton Town | ||||
| Tue | Sep | 5 | Northampton Town | 0 | - | 2 | Mansfield Town | ||||
| Mansfield won 3-1 on aggregate | |||||||||||
| Wed | Aug | 23 | Peterborough United | 2 | - | 0 | Aldershot | ||||
| Tue | Aug | 29 | Aldershot | 6 | - | 2 | Peterborough United | ||||
| Aldershot won 6-4 on aggregate | |||||||||||
| Tue | Aug | 22 | Preston North End | 3 | - | 4 | Tranmere Rovers | ||||
| Tue | Aug | 29 | Tranmere Rovers | 3 | - | 1 | Preston North End | ||||
| Tranmere won 7-4 on aggregate | |||||||||||
| Tue | Aug | 22 | Rochdale | 2 | - | 1 | Bolton Wanderers | ||||
| Tue | Aug | 29 | Bolton Wanderers | 5 | - | 1 | Rochdale | ||||
| Bolton won 6-3 on aggregate | |||||||||||
| Wed | Aug | 23 | Scarborough | 2 | - | 0 | Scunthorpe United | ||||
| Tue | Aug | 29 | Scunthorpe United | 1 | - | 1 | Scarborough | ||||
| Scarborough won 3-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Sheffield United | 1 | - | 1 | Rotherham United | ||||
| Tue | Aug | 29 | Rotherham United | 1 | - | 0 | Sheffield United | ||||
| Rotherham won 2-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Shrewsbury Town | 3 | - | 0 | Notts County | ||||
| Tue | Aug | 29 | Notts County | 3 | - | 1 | Shrewsbury Town | ||||
| Shrewsbury won 4-3 on aggregate | |||||||||||
| Mon | Aug | 21 | Stockport County | 1 | - | 0 | Bury | ||||
| Tue | Aug | 29 | Bury | 1 | - | 1 | Stockport County | ||||
| Stockport won 2-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Torquay United | 0 | - | 1 | Hereford United | ||||
| Wed | Aug | 30 | Hereford United | 3 | - | 0 | Torquay United | ||||
| Hereford won 4-0 on aggregate | |||||||||||
| Tue | Aug | 22 | Walsall | 1 | - | 2 | Port Vale | ||||
| Mon | Aug | 28 | Port Vale | 1 | - | 0 | Walsall | ||||
| Port Vale won 3-1 on aggregate | |||||||||||
| Tue | Aug | 22 | Wolverhampton Wanderers | 1 | - | 0 | Lincoln City | ||||
| Wed | Aug | 30 | Lincoln City | 0 | - | 2 | Wolverhampton Wanderers | ||||
| Wolves won 3-0 on aggregate | |||||||||||
| Tue | Aug | 22 | Wrexham | 0 | - | 0 | Wigan Athletic | ||||
| Tue | Aug | 29 | Wigan Athletic | 5 | - | 0 | Wrexham | ||||
| Wigan won 5-0 on aggregate | |||||||||||
|  |  |  |  |  |  |  |  |  |  |  |   | 
| Second Round | |||||||||||
| Tue | Sep | 19 | Arsenal | 2 | - | 0 | Plymouth Argyle | ||||
| Tue | Oct | 3 | Plymouth Argyle | 1 | - | 6 | Arsenal | ||||
| Arsenal won 8-1 on aggregate | |||||||||||
| Wed | Sep | 20 | Aston Villa | 2 | - | 1 | Wolverhampton Wanderers | ||||
| Wed | Oct | 4 | Wolverhampton Wanderers | 1 | - | 1 | Aston Villa | ||||
| Aston Villa won 3-2 on aggregate | |||||||||||
| Tue | Sep | 19 | Barnsley | 1 | - | 1 | Blackpool | ||||
| Tue | Oct | 3 | Blackpool | 1 | - | 1 | Barnsley | ||||
| Blackpool won 5-4 on penalties after finishing 2-2 on aggregate | |||||||||||
| Tue | Sep | 19 | Birmingham City | 1 | - | 2 | West Ham United | ||||
| Wed | Oct | 4 | West Ham United | 1 | - | 1 | Birmingham City | ||||
| West Ham won 3-2 on aggregate | |||||||||||
| Tue | Sep | 19 | Bolton Wanderers | 2 | - | 1 | Watford | ||||
| Tue | Oct | 3 | Watford | 1 | - | 1 | Bolton Wanderers | ||||
| Bolton won 3-2 on aggregate | |||||||||||
| Tue | Sep | 19 | Brentford | 2 | - | 1 | Manchester City | ||||
| Wed | Oct | 4 | Manchester City | 4 | - | 1 | Brentford | ||||
| Manchester City won 5-3 on aggregate | |||||||||||
| Tue | Sep | 19 | Cambridge United | 2 | - | 1 | Derby County | ||||
| Wed | Oct | 4 | Derby County | 5 | - | 0 | Cambridge United | ||||
| Derby won 6-2 on aggregate | |||||||||||
| Wed | Sep | 20 | Charlton Athletic | 3 | - | 1 | Hereford United | ||||
| Wed | Oct | 4 | Hereford United | 0 | - | 1 | Charlton Athletic | ||||
| Charlton won 4-1 on aggregate | |||||||||||
| Tue | Sep | 19 | Chelsea | 1 | - | 1 | Scarborough | ||||
| Wed | Oct | 4 | Scarborough | 3 | - | 2 | Chelsea | ||||
| Scarborough won 4-3 on aggregate | |||||||||||
| Tue | Sep | 19 | Crewe Alexandra | 0 | - | 1 | Bournemouth | ||||
| Tue | Oct | 3 | Bournemouth | 0 | - | 0 | Crewe Alexandra | ||||
| Bournemouth won 1-0 on aggregate | |||||||||||
| Tue | Sep | 19 | Crystal Palace | 1 | - | 2 | Leicester City | ||||
| Wed | Oct | 4 | Leicester City | 2 | - | 3 | Crystal Palace | ||||
| Crystal Palace won on away goals after finishing 4-4 on aggregate | |||||||||||
| Wed | Sep | 20 | Exeter City | 3 | - | 0 | Blackburn Rovers | ||||
| Tue | Oct | 3 | Blackburn Rovers | 2 | - | 1 | Exeter City | ||||
| Exeter won 4-2 on aggregate | |||||||||||
| Tue | Sep | 19 | Grimsby Town | 3 | - | 1 | Coventry City | ||||
| Wed | Oct | 4 | Coventry City | 3 | - | 0 | Grimsby Town | ||||
| Coventry won 4-3 on aggregate | |||||||||||
| Tue | Sep | 19 | Ipswich Town | 0 | - | 1 | Tranmere Rovers | ||||
| Tue | Oct | 3 | Tranmere Rovers | 1 | - | 0 | Ipswich Town | ||||
| Tranmere won 2-0 on aggregate | |||||||||||
| Tue | Sep | 19 | Leyton Orient | 0 | - | 2 | Everton | ||||
| Tue | Oct | 3 | Everton | 2 | - | 2 | Leyton Orient | ||||
| Everton won 4-2 on aggregate | |||||||||||
| Tue | Sep | 19 | Liverpool | 5 | - | 2 | Wigan Athletic | ||||
| Wed | Oct | 4 | Wigan Athletic | 0 | - | 3 | Liverpool | ||||
| Liverpool won 8-2 on aggregate | |||||||||||
| Tue | Sep | 19 | Mansfield Town | 3 | - | 4 | Luton Town | ||||
| Tue | Oct | 3 | Luton Town | 7 | - | 2 | Mansfield Town | ||||
| Luton won 11-5 on aggregate | |||||||||||
| Wed | Sep | 20 | Middlesbrough | 4 | - | 0 | Halifax Town | ||||
| Tue | Oct | 3 | Halifax Town | 0 | - | 1 | Middlesbrough | ||||
| Middlesbrough won 5-0 on aggregate | |||||||||||
| Wed | Sep | 20 | Norwich City | 1 | - | 1 | Rotherham United | ||||
| Tue | Oct | 3 | Rotherham United | 0 | - | 2 | Norwich City | ||||
| Norwich won 3-1 on aggregate | |||||||||||
| Wed | Sep | 20 | Nottingham Forest (holders) | 1 | - | 1 | Huddersfield Town | ||||
| Tue | Oct | 3 | Huddersfield Town | 3 | - | 3 | Nottingham Forest (holders) | ||||
| Nottingham Forest won on away goals after finishing 4-4 on aggregate | |||||||||||
| Tue | Sep | 19 | Oldham Athletic | 2 | - | 1 | Leeds United | ||||
| Tue | Oct | 3 | Leeds United | 1 | - | 2 | Oldham Athletic | ||||
| Oldham won 4-2 on aggregate | |||||||||||
| Mon | Sep | 18 | Port Vale | 1 | - | 2 | Wimbledon | ||||
| Wed | Oct | 4 | Wimbledon | 3 | - | 0 | Port Vale | ||||
| Wimbledon won 5-1 on aggregate | |||||||||||
| Wed | Sep | 20 | Portsmouth | 2 | - | 3 | Manchester United | ||||
| Tue | Oct | 3 | Manchester United | 0 | - | 0 | Portsmouth | ||||
| Manchester United won 3-2 on aggregate | |||||||||||
| Wed | Sep | 20 | Queens Park Rangers | 2 | - | 1 | Stockport County | ||||
| Mon | Oct | 2 | Stockport County | 0 | - | 0 | Queens Park Rangers | ||||
| QPR won 2-1 on aggregate | |||||||||||
| Tue | Sep | 19 | Reading | 3 | - | 1 | Newcastle United | ||||
| Wed | Oct | 4 | Newcastle United | 4 | - | 0 | Reading | ||||
| Newcastle won 5-3 on aggregate | |||||||||||
| Wed | Sep | 20 | Sheffield Wednesday | 0 | - | 0 | Aldershot | ||||
| Tue | Oct | 3 | Aldershot | 0 | - | 8 | Sheffield Wednesday | ||||
| Sheffield Wednesday won 8-0 on aggregate | |||||||||||
| Tue | Sep | 19 | Shrewsbury Town | 0 | - | 3 | Swindon Town | ||||
| Tue | Oct | 3 | Swindon Town | 3 | - | 1 | Shrewsbury Town | ||||
| Swindon won 6-1 on aggregate | |||||||||||
| Tue | Sep | 19 | Stoke City | 1 | - | 0 | Millwall | ||||
| Tue | Oct | 3 | Millwall | 2 | - | 0 | Stoke City | ||||
| Millwall won 2-1 on aggregate | |||||||||||
| Tue | Sep | 19 | Sunderland | 1 | - | 1 | Fulham | ||||
| Tue | Oct | 3 | Fulham | 0 | - | 3 | Sunderland | ||||
| Sunderland won 4-1 on aggregate | |||||||||||
| Wed | Sep | 20 | Tottenham Hotspur | 1 | - | 0 | Southend United | ||||
| Wed | Oct | 4 | Southend United | 3 | - | 2 | Tottenham Hotspur | ||||
| Spurs won on away goals after finishing 3-3 on aggregate | |||||||||||
| Wed | Sep | 20 | West Bromwich Albion | 1 | - | 3 | Bradford City | ||||
| Wed | Oct | 4 | Bradford City | 3 | - | 5 | West Bromwich Albion | ||||
| WBA won on away goals after finishing 6-6 on aggregate | |||||||||||
| Wed | Sep | 20 | York City | 0 | - | 1 | Southampton | ||||
| Tue | Oct | 3 | Southampton | 2 | - | 0 | York City | ||||
| Southampton won 3-0 on aggregate | |||||||||||
| Third Round | |||||||||||
| Wed | Oct | 25 | Arsenal | 1 | - | 0 | Liverpool | ||||
| Wed | Oct | 25 | Aston Villa | 0 | - | 0 | West Ham United | ||||
| Wed | Nov | 8 | West Ham United | 1 | - | 0 | Aston Villa | ||||
| Tue | Oct | 24 | Crystal Palace | 0 | - | 0 | Nottingham Forest (holders) | ||||
| Wed | Nov | 1 | Nottingham Forest (holders) | 5 | - | 0 | Crystal Palace | ||||
| Wed | Oct | 25 | Derby County | 2 | - | 1 | Sheffield Wednesday | ||||
| Tue | Oct | 24 | Everton | 3 | - | 0 | Luton Town | ||||
| Wed | Oct | 25 | Exeter City | 3 | - | 0 | Blackpool | ||||
| Wed | Oct | 25 | Manchester City | 3 | - | 1 | Norwich City | ||||
| Wed | Oct | 25 | Manchester United | 0 | - | 3 | Tottenham Hotspur | ||||
| Wed | Oct | 25 | Middlesbrough | 1 | - | 1 | Wimbledon | ||||
| Wed | Nov | 8 | Wimbledon | 1 | - | 0 | Middlesbrough | ||||
| Wed | Oct | 25 | Newcastle United | 0 | - | 1 | West Bromwich Albion | ||||
| Wed | Oct | 25 | Oldham Athletic | 7 | - | 0 | Scarborough | ||||
| Wed | Oct | 25 | Queens Park Rangers | 1 | - | 2 | Coventry City | ||||
| Tue | Oct | 24 | Southampton | 1 | - | 0 | Charlton Athletic | ||||
| Tue | Oct | 24 | Sunderland | 1 | - | 1 | Bournemouth | ||||
| Tue | Nov | 7 | Bournemouth | 0 | - | 1 | Sunderland | ||||
| Tue | Oct | 24 | Swindon Town | 3 | - | 3 | Bolton Wanderers | ||||
| Tue | Nov | 7 | Bolton Wanderers | 1 | - | 1 | Swindon Town | ||||
| Tue | Nov | 14 | Bolton Wanderers | 1 | - | 1 | Swindon Town | ||||
| Tue | Nov | 21 | Swindon Town | 2 | - | 1 | Bolton Wanderers | ||||
| Mon | Oct | 23 | Tranmere Rovers | 3 | - | 2 | Millwall | ||||
| Fourth Round | |||||||||||
| Wed | Nov | 22 | Derby County | 2 | - | 0 | West Bromwich Albion | ||||
| Wed | Nov | 29 | Exeter City | 2 | - | 2 | Sunderland | ||||
| Tue | Dec | 5 | Sunderland | 5 | - | 2 | Exeter City | ||||
| Wed | Nov | 22 | Manchester City | 0 | - | 1 | Coventry City | ||||
| Wed | Nov | 22 | Nottingham Forest (holders) | 1 | - | 0 | Everton | ||||
| Wed | Nov | 22 | Oldham Athletic | 3 | - | 1 | Arsenal | ||||
| Wed | Nov | 29 | Swindon Town | 0 | - | 0 | Southampton | ||||
| Tue | Jan | 16 | Southampton | 4 | - | 2 | Swindon Town | ||||
| Wed | Nov | 22 | Tranmere Rovers | 2 | - | 2 | Tottenham Hotspur | ||||
| Wed | Nov | 29 | Tottenham Hotspur | 4 | - | 0 | Tranmere Rovers | ||||
| Wed | Nov | 22 | West Ham United | 1 | - | 0 | Wimbledon | ||||
| Fifth Round | |||||||||||
| Wed | Jan | 17 | Nottingham Forest (holders) | 2 | - | 2 | Tottenham Hotspur | ||||
| Wed | Jan | 24 | Tottenham Hotspur | 2 | - | 3 | Nottingham Forest (holders) | ||||
| Wed | Jan | 24 | Southampton | 2 | - | 2 | Oldham Athletic | ||||
| Wed | Jan | 31 | Oldham Athletic | 2 | - | 0 | Southampton | ||||
| Wed | Jan | 17 | Sunderland | 0 | - | 0 | Coventry City | ||||
| Wed | Jan | 24 | Coventry City | 5 | - | 0 | Sunderland | ||||
| Wed | Jan | 17 | West Ham United | 1 | - | 1 | Derby County | ||||
| Wed | Jan | 24 | Derby County | 0 | - | 0 | West Ham United | ||||
| Wed | Jan | 31 | West Ham United | 2 | - | 1 | Derby County | ||||
| Semi-Finals (home and away legs) | |||||||||||
| Sun | Feb | 11 | Nottingham Forest (holders) | 2 | - | 1 | Coventry City | ||||
| Sun | Feb | 25 | Coventry City | 0 | - | 0 | Nottingham Forest (holders) | ||||
| Nottingham Forest won 2-1 on aggregate | |||||||||||
| Wed | Feb | 14 | Oldham Athletic | 6 | - | 0 | West Ham United | ||||
| Wed | Mar | 7 | West Ham United | 3 | - | 0 | Oldham Athletic | ||||
| Oldham won 6-3 on aggregate | |||||||||||
| Final (at Wembley Stadium, London) | |||||||||||
| Sun | Apr | 29 | Nottingham Forest (holders) | 1 | - | 0 | Oldham Athletic | ||||
|   | Question: | 
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